winter suits

A Gentleman’s Guide to Winter Suits Everything you need to know when shopping for winter suiting

Written by RJ Firchau

When the icy chill of winter rears its frosty head, it’s time to push your linen and seersucker suits to the back of the closet and opt for something bit warmer. Suit fabrics make all the difference when you’re forced to bear the cold while managing to look sharp.

However, winter suiting does not have to be boring. In the same way that the warm summer weather gave you a surfeit of outfit flexibility in the form of summer suits, you can apply the same creativity and style to your cold-weather ensembles.

Look cool and stay warm all winter long. Here is our definitive guide on what to look for in a winter suit.

What to Look for in a Winter Suit

If anyone tries to sell you a suit claiming that it’s suitable for year-round wear, grab your money and run. A fabric that is breathable and lightweight in the summer will make you miserable in the winter, and vice versa.

winter suit guide

TM Lewin

Unless you live in a very temperate climate, you should have a designated selection of suits for, at the very least, summer and winter. For the best winter suit, pay attention to the suit’s construction and fabric. These factors will determine the suit’s ability to keep you warm.

Depending on how cold it gets where you live, be sure to stick to half- or fully-lined suit jackets. Lined jackets will resist wrinkles, retain warmth, and hold up better during travel and everyday wear than unlined suits. Here are some of the best fabrics, colors, and patterns for winter suiting.


The optimal winter suit will be made of a warmer, thicker fabric that will keep you nice and toasty against the elements. Stay away from the lighter suit fabrics like cotton, polyester, linen, seersucker, chambray, and fresco, as these will induce endless shivering. Unlike summer suits, winter fabric better lends itself to retaining a suit’s shape and maintain their structure exceptionally well, so you won’t have to worry as much about wrinkling or wearing of material.

The Wool Suit

To this day, wool remains the most popular suit fabric. Wool is a fabric renowned for its ability to drape nicely, maintain its form, and its versatility in being able to be spun as loose and breathable or tight and warm as necessary. Wool suits have maintained the position of being the most popular suit on the market for decades, because of these versatile qualities.

winter suit wool suit

Trashness / GQ

This is a great place to start acquiring your winter suiting, as a good wool suit is easy to find and comes in a variety of types. Worsted wool is the most popular wool used for suits, as it is highly adaptable to temperature change, wears well, and gives off that slight shine that you find in most suits on the market. Other popular types of wool are tweed and flannel. Worsted is considered mid-weight wool, tweed is heavier, and flannel is the heaviest. Flannel and tweed are discussed in greater detail below.

The Cashmere Suit

Arguably one of the most coveted and luxurious suit fabrics on the market, cashmere is known for its unparalleled soft texture, comfort, and most importantly warmth. However, some of the biggest drawbacks for this fabric is its price tag and its lack of durability.

winter suit cashmere suit

Jacket Designs / Paul Smith

Rather than shelling out thousands for a 100% cashmere suit that won’t last you very long, opt for a wool or polyester blend. Blends keep cashmere prices low while giving you the advantage of other fabrics’ durability. Along with being soft, cashmere is also amazing for keeping you consistently warm. The fabric is highly adaptable to climate change and will be able to insulate you very well.

However, be very particular about how you store your suit because cashmere attracts moths, who can chew $1,000 holes into your suits quicker than you will be able to wear them. If you do decide on a cashmere or cashmere blend suit, protect your purchase with a cedar closet or mothballs.

The Tweed Suit

Tweed is a great winter suit fabric that will always give timeless ease to the wearer. The fabric is made from wool and created by combining three differently colored yarns, which are then twilled.

winter suit tweed suit

Jennis & Warmann / Hawes & Curtis

To “twill” is to weave yarn in such a way that it produces a distinctive pattern unique only to this variety of fabric. Tweed makes a fine winter suit choice because it is thick, warm, water resistant, and durable. However, tweed suits are a little heavier compared with most suits, and the fabric is coarse to the touch. If you live in a very cold winter climate and you don’t mind the feel of the fabric, a tweed suit is definitely the way to go to make a classic statement.

The Flannel Suit

Another winter suit fabric is flannel, which was made for protecting against cold climates. Traditionally speaking, flannel suits are for more mature gentlemen. But flannel is increasingly reinventing itself as a suit fabric for the bold and stylish modern man.

winter suit flannel suit

Gentleman’s Gazette / French Connection

Though these suits are weather appropriate, they aren’t always comfortable in an office environment because of their weight. Flannel is typically made of worsted wool. It is similar to tweed and herringbone in terms of look, but it’s softer to the touch. These suits have the advantage of being hip and stylish, giving wearers a polished and slightly felted appearance. Flannel also appears the most luxurious of the heavier fabrics because it is extremely soft. However, flannel suits are a bit tougher to find, and you can expect to pay a pretty penny ($800-$2000) to get your hands on one.

If you can afford a flannel suit, having one in your winter arsenal will show the world that you are able to curate your look appropriately with the changing seasons and that you are a style trendsetter. Flannel is acceptable for day-to-day use, but may not be formal enough for special occasions or strict dress codes.

The Herringbone Suit

Much like tweed, the herringbone is heavy, warm, and durable. What distinguishes herringbone from tweed is a distinctive thin zig-zag pattern.

winter suit herringbone suit

Astute Attire / Gianni Feraud

Like tweed, herringbone suits are made from twilled yarn, typically from materials like wool or flannel. Both tweed and herringbone fabrics consist of a tighter weave than most suits, making for a more structured and durable garment. The thickness of the fabric paired with the subtle zig-zag design cause this suit to give off an illusion of depth, making this suit ideal for gentlemen on the slimmer side.


It’s great to have some all-season suit staples in black, navy, or charcoal. However, just because the winter is prime time for darker hues, this does not mean you can’t also have a little fun with color. If you already have your suit staples in check, try implementing some of these daring options into your winter wardrobe. Feel free to go bold with a full suit in one of these colors, or break it up with a colored jacket, pants, or accessories.


winter suit color oxblood

Men’s Style Pro / ASOS

Definitely not your average black, gray, or navy suit, oxblood suits are popping up everywhere these days. What exactly is oxblood? Oxblood is a deep shade of burgundy, a shade that commands presence and attention when you walk into a room while maintaining a suit’s formal essence. It is bold enough to make a statement but not so loud that it isn’t office appropriate.

Hunter Green

winter suit color hunter green

DH Gate / Lookastic

Another great color that makes a statement without coming off forced is hunter green. This particular shade of dark green looks great and is a classy alternative to the traditional neutral tones. Slightly jewel-toned in hue, but still deep and reserved, you’d be hard-pressed NOT to include this color in your arsenal this winter.


winter suit color cognac

Jack London / Vogue

Though brown is also on trend for the fall and winter months, how about trying its caramel-y, amber cousin instead? A neutral color that is more modern than the traditional brown and more stylish than, let’s say, khaki, a cognac suit will impress your coworkers without attracting any wayward looks from the boss. Cognac is a perfect suit color for those looking to add a unique element to their ensemble without being overstated.


winter suit color plum

Marie Claire / DH Gate

Deep, deep purple on a suit will be sure to give you an edge to stand out. Like oxblood, plum is a bold color choice, so wear it with pride, and you’ll be sure to look like a true connoisseur of style.

winter suit accessories

Just because it’s winter does not mean you can’t have fun with your style. Your winter suit colors tend to be darker. Choose accessories that either complement (dark hues) or contrast (bright, patterned) your suit for a big impact. Feel free to play up textures and patterns to add dimension to your look.

Knit ties are a great seasonal accessory for winter and generally look great with everything. Scarves are a winter essential that also adds style and will keep you warm on your way to and from the office. Finally, try adding some floral to your ensemble. Dark florals are definitely happening for winter. Achieve this trend with a floral tie, simple dark floral button up, or even a floral pocket square. Remember, you don’t have to stick to dark, subdued hues just because it’s winter. Add style and dimension to your winter look through accessories, and have fun with it.



What Does Your Bag Say About You?Your bag of choice may say more about you than you realise

Written by RJ Firchau

Bags are as essential of a component in shaping your everyday style as they are for women. However, for a lot of us, the bag that we end up toting around every day is often an afterthought, regarded only in terms of function and hardly (if ever) in terms of form. Perhaps your trustworthy backpack, which has served you well over the years with its myriad compartments and sheer resilience (consider how many times have you torn and thrown it around, and it still hasn’t broken? Impressive), is your go-to through thick and thin

Or maybe you like to throw all your belongings into a drawstring sack because it is easy, a no-brainer (who needs compartments, or style, anyway), and it’ll make you look like you frequent the gym daily. We’ve talked about different bag types before, but not about what your bag preference means.

It’s clear that the bag you choose says a lot about you, whether you like it or not. Further, your bag choice can sabotage your entire look, especially when it is an afterthought. We get it. Bags were meant to be functional.–to help you get your stuff from point A to point B. But that doesn’t mean you have to sacrifice style. Here is precisely what your bag says about you, as well as a couple of recommendations for bags that marry function with style, too.


Leather Messenger Bag

Best For: Travel, Business, and The Art of Looking Like You Have a Job

Messenger bags have been around for over a century and were originally popularized by dispatchers during WWII, who would use them to carry messages on horseback. To make accessing the bag’s contents easy, a cross-body style with a large opening flap was adapted, and that style stuck. Today, the bag is known for being durable, convenient, and stylish, especially for commuters. If a leather messenger bag is your carrier of choice, it means you are a professional who is always on the go but still cares about aesthetics (if you didn’t, you’d be just another backpack carrier, and where’s the fun in that?). 

Canvas Courier

Best For: Work, Study, Commuting

Just like the previous bag, a canvas or nylon messenger means that you are a style-savvy commuter. Based on your bag preference, you are probably either a student or a young professional, and you commute, most likely on a motorcycle (and if you don’t, you enjoy the fact that this bag makes you look like you do). You’re mildly rugged, and you chose a bag that could withstand anything and roll with the punches. Through thick and thin, this bag has been with you. The scratches and minor tears are simply reminders of your adventurous (or clumsy?) nature. 

Leather Briefcase

Best For: Business, Work, Meetings

A tried and true classic. You are a professional and want to be regarded as such. This bag says to the world that you are a businessman by trade, and that you don’t take no for an answer. You’re a driven, educated individual who thrives on organization. If you don’t work at a fortune 500 company and carry a degree from Yale, you certainly pull off the look well, at least. 


Best For: Business, Looking Important

You’re on a secret mission transporting top-secret classified documents to their final destination. Okay, maybe you’re not actually doing that, but you sure look like it. Hard briefcases–either made of aluminum or leather, usually–are formal and classic, albeit a little stuffy. You mean business, and you’re not afraid to let it show. All pretenses aside, attaches are great for keeping your documents safe, as the solid structure doesn’t allow for folding or wrinkling. 

Zip-Up Backpack

Best For: Commuting, Working Out, Studying

Backpacks have their place, but if you’re carrying a backpack around as an everyday commuter bag, you’re treading the fine line between positive and negative connotations. If you’re under 23, okay, fine, it’s a youthful, functional bag and it’s serving its purpose. If you’re older, though, it looks like you either don’t have your life together or you aren’t actively trying to pursue bigger and better things. Ditch the backpack instead for a rucksack (mildly nicer) or a messenger back for a vessel that’s still functional but not without its added style points. 

Heritage or Leather Rucksack

Best For: (Looking slightly more stylish while) Commuting, Working Out, Studying

A step above the standard backpack, you still value function over style but you’re not blind to the fact that these backpacks look great, and you intentionally chose it with that in mind. These bags are best worn with beards, flannels, and chukkas. 


Best For: Commuting, Transporting Things

Totes can be really hit or miss. However, you can’t deny their ability to, you know, carry stuff. If the tote is your bag of choice, it’s either a style or eco-conscious choice, most likely. If it’s the latter, it could be safe to assume you wear Toms and frequent farmers markets every Saturday morning (nothing wrong with that).


Best For: Weekend Travel, Short Trips (carry-on only)

Always on the go, you and your weekender bag have been places. Weekenders are stylish, convenient, and have just the right amount of space for all of your needs (think the Mary Poppins purse of men’s bags). Whether you’re a commuter or a jetsetter, a weekender bag is a classy choice, which makes you a classy person by extension. 


Best For: Weekend Travel, Short Trips (carry-on only), Working Out

Much like a weekender but, depending on the make, perhaps a little less stylish, the duffel bag is made to fit a wide variety of needs, whether they be going to the gym or packing for a week-long vacation. If the duffel is your everyday bag of choice, you probably look like a workout buff, or a guy who’s always going places. Hey, you gotta carry your essentials from point a to point b somehow. 


Best For: Travel

More durable than a duffel or a weekender, but arguably a little less “cool,” roller bags are all about function. Yes, you can find some really sleek, minimalistic variations these days, but if it has wheels on it, the perception is still the same. Roller bags are 100% perfect for vacations that span longer than the weekend. But if you use your roller every day, you may look like a teacher or a librarian (which is cool, if that’s your thing).


Best For: Working Out, Doing Outdoor Things

Sack, or drawstring, bags serve a strictly functional purpose. They’re great for going to the gym, hitting the trails, or heading to the beach. As an everyday bag, it’ll probably make you look like a total bro or a gym buff, and if that’s your thing, more power to you. 


Best For: Travel, Sightseeing

Satchels are definitely for the more adventure-prone gentlemen. Harkening images of Indiana Jones and monument-trekking tourists, satchels scream “vagabond.” Whether you use yours for crazy cross-country journeys or just to carry your work stuff around with you, a satchel is perfect for any guy who wants to look like he has a wild and free, yet still style conscious, persona.

check our in-store range of bags here

Bow Ties

Bow Ties 101: An Introduction to Bow TiesEverything you need to know to knot up

Written by Jennifer Song

Confidence and sophistication — a man in a bow tie radiates both. Unless of course he has chosen the wrong bow tie or worn a bow tie with the wrong ensemble. In that case, the bow tie renders his entire costume pagliaccio.

Such mistakes are avoidable, however, and the proposition a bow tie makes to a man is a simple one: Are you going for Bond, James Bond or Laugh, clown, laugh?

bow tie primer

The original

The question matters, because – sooner or later – every thinking man discovers for himself that wearing the right bow tie is the nicest thing he can do for his shirt, suit, and style. When one’s ensemble features or is constructed around a well-chosen bow tie, there’s no sharper way to step-out. Sometimes a bow tie is de rigueur, but a bow tie is always a bold and emboldening selection. We hope our guide will leave you shaken and stirred about the bow tie, and keen to begin experimenting — or perhaps adding to your collection.

Where Did the Bow Tie Originate?

The bow tie has Croatian roots reaching at least as far back as the 17th century. Croatian mercenaries used a type of neckwear (similar to a short scarf) to hold together the collars of their shirts.   This article was known as a Hvrat, which is Croatian for “Croatian” (or, Croat).  Cravate – which is French for Croat – eventually becamecravat. The short scarf of the Cravates was assimilated by the French upper-sets, to whom Europeans of the period looked as arbiters of fashion. In due course, the many types of cravat out there evolved into the predecessors of the men’s neckwear we know today: bow ties and neckties. The former emerged as an essential part of formal attire, and by the 1900s a bow tie was a staple item in the Everyman’s wardrobe. In the decades subsequent to the end of World War II, the bow tie became less common; but even when popularity ebbed it remained (and does still remain) a fixture of formal attire.

Croatians Celebrating Cravat Day

Croatians Celebrating Cravat Day

Although it never vanished completely from menswear, the bow tie has once again begun to reassert itself as a staple. We are happy to say that an ever-growing number of style-conscious men are now comfortable incorporating bow ties into their day-to-day outfits, and no longer view the bow tie as the preserve of the quirky, the comic, or the contrived. This is a point that we believe deserves emphasis. A man should feel as comfortable switching between neckties and bow ties as he would between monk-straps and lace-ups or between belts and braces.

What’s the Difference Between Self-Tie, Pre-Tied & Clip-On Bow Ties?

Bow Tie Types

The Self-Tie Bow Tie

Bow ties proper are of course “self-tie” bow ties.  They have become known also as “freestyle” bow ties, but this we think is only a clever way of raising the status of other bow ties. “Self-tie” means exactly what you think: you tie the bow yourself.

And herein lies 90% of its charm. Once tied, the bow’s natural lines, shape, and slight asymmetry bring to the shirt (and to a man’s upper-half) elements that cannot be matched by a pre-tied bow, or a necktie. The ineluctable imprecision of the (self-tied) bow tie may be the counterpoint to the immaculacy of an ensemble, or it may be of a piece with the managed carelessness of one.

Learning to tie one properly is no great affair, but it does require some patience and a bit of practice.  Opinion is divided as to whether wearing an untied bow tie around one’s collar is debonaire or a silly affectation. We say: if you’ve loosened the knot at day’s end – or: if the bow has been tugged-free by someone planning on unwrapping you like a present – then the untied and free-hanging bow tie it is an outstanding look. To perch an untied bow tie on one’s nape and dangle it from the collar – absent any intention of tying it – is de trop.

The Pre-Tied Bow Tie

The pre-tied bow tie is a neat, preternaturally symmetrical bow attached to an adjustable band. It is easy to size-to-fit,  and painless to put-on. Pre-tied bow ties look pre-tied, and lack the character as a self-tie. The pre-tied bow tie is suitable for children, and for those who lack or no longer have the dexterity to tie or adjust for themselves a self-tie. We do not recommend the pre-tied bow tie as a “starter” bow tie. A style-conscious and nuance-sensitive man will detect that the look of his pre-tied bow tie is somehow off, and that his appearance with it on is less impressive than he imagined.

The Clip-On Bow Tie

This is a pre-tied bow attached to a metal clasp which hooks or clips directly onto the collar of a shirt. Clip-on bow ties are suitable for young children only. Period.

Sizing Your Bow Tie

A bow tie is, with limited exception, a one-size-fits-all affair. With a little trial and error, any adjustable bow tie can be made to fit the neck of the average adult male. The band/neck strap of a bow tie typically has either an adjustable slider or a hook-and-holes arrangement with pre-marked measurements. Bow ties can generally accommodate collar sizes between 14.5 inches to 17.5 inches. If your bow tie has the hook-and-hole adjustment system, match the sizing to the size of the collar of the shirt you will be wearing. If your bow tie has a sliding-adjustment system, we recommend the following. With upturned collar wrap the tie around the collar band as if you are preparing to tie it (see below).  At the topmost button of your shirt, cross the two ends of the tie — just as if you were going to tie it in a simple overhand knot.  The length of each of the tie’s end bits should appear long enough to execute a bow but should not seem too long. How long is “too long”? It is difficult to say, but the distance between the crisscrossed part of the tie (at the top button) and the start of your bow tie’s flared part should not be more than three fingers’ width. Adjustment is inevitable, and practice is necessary.   

How to Tie a Bow Tie

Learning how to tie a bow tie is regarded by some as a rite of passage on the journey to becoming a true gentleman. Tying a bow can be difficult the first few times and takes practice to master. has made the job a little easier with this easy to follow bow tie infographic.

Five Bow Tie Shapes You Should Know

Know Your Bow Tie Shapes

The Butterfly

The modern butterfly, also known as the thistle shape, is the style of bow tie with which most people are familiar. This butterfly is appropriate for virtually every occasion and is perhaps the best style to acquire first if you are beginning to experiment with bow ties. We believe that every man’s tie collection should have at least one butterfly bow tie.

The Big Butterfly

The big butterfly is larger and has a more relaxed silhouette than the butterfly.  It is sometimes worn with formalwear and is perhaps best-suited to fancy-dress occasions. The style is very appropriate for larger and/or taller men. Absent a suitable context, or on a smaller man, the big butterfly can look comic. It is a grandiose tie, and should, therefore, be worn grandly.

The Batwing

The batwing shape, also known as a straight or slim bow tie, is the smallest in height. Untied, this style looks like a long rectangle strip with flat ends. Batwing bow ties are typically less than two inches in width. Tied well, they provide a clean, symmetrical look. Some regard it as less formal than the butterfly, but it is a classic shape and remains acceptable for black tie events. Be sure not to tie it too long, or it will look like you are wearing a propeller.

The Diamond Point

The diamond tip bow tie has pointed ends, and when tied is delightfully asymmetrical. It is one of our favorite styles.

The Rounded Club

These days the rounded club bow is the rara avis of the bow ties. Arguably the least formal of the lot, this is the tie for a Sunday run in the Mitsuoka Himiko, a picnic by the lake, or a spot of angling on the Tay. We like this style and like it best in cotton and rougher textiles.

When is a Bow Tie the Right Tie?

A bow tie is rarely the wrong tie to wear — provided you have chosen the right one for your ensemble, the ensemble is occasion-appropriate, you have tied your tie well, and you wear it with ease and nonchalance.

Formal Attire

Weddings apart, one of the most common places to see a bow tie in action is a formal engagement — the black-tie-only event for which few of us have regular invites to. This dress code for these is relatively straightforward and unambiguous: dinner jacket (tuxedo) and a black bow tie, preferably in silk. Wearing a self-tie bow tie to these is important: a pre-tied bow tie looks pre-tied and diminishes both you and your ensemble. A white tie event is yet a further notch up — perhaps the ne plus ultra of formal. Known sometimes as “full dress,” white tie is the most formal of all dress codes. As the name suggests, a white bow tie (always a self-tie) is absolutely necessary. This is not the time to experiment with colors. See our complete breakdown of the formal dress codes.

Semi-Formal Attire

Notwithstanding the fact that the very phrase semi-formal is vexing, any affair so-billed is a wonderful occasion for experimentation with bow ties. We do not recommend taking too much license with your ensemble: it is better, we think, to lean towards formal than list towards semi. By all means enjoy your options with respect to bow tie styles, materials, and textures; but your aim is to remain aligned with a dress code, so do resist the temptation to get too creative.

Casual Attire

“Casual” dress codes (and the absence of a dress code) liberates you to rewrite the rules if you wish to do so. First-time bow tie wearers may incline towards supporting accessories like braces (suspenders,) printed socks, and bright shoelaces. We recommend not getting carried away or going in period-costume — unless that’s your thing.

Choosing your ensemble is only half the battle. The best thing you can wear with your bow tie is confidence. Too often, bow ties will wear the man, instead of the other way around.

Check our latest in bow ties here

shoe guide

The Ultimate Men’s Dress Shoe GuideThe anatomy and style of classic men’s dress shoes.

Written by Jacob Sigala

Having a great pair of dress shoes in your closet is not a luxury, it’s a necessity. Even men who default to casual shoes and sneakers will eventually need to suit-up. Opportunity favors the prepared.

This guide is intended to help you make a wiser choice on your next shoe purchase. Once you understand the differences between the options available, you will be half-way to looking your best at any event, interview, meeting, or date that requires a formal shoe.

Take the quiz: What shoes should you wear with your outfit? 

Deconstructing the Dress Shoe

vamp, upper, sole, quarters, facing, toe, heel

In order to understand a particular style, you should first understand the components that make up a dress shoe. Working from front to back, a dress shoe is divided into four parts: toevampfacing, and quarter. It is the placement and construction of these pieces that help give a dress shoe its individuality.


The Oxford

The Ultimate Guide to Dress Shoes: Oxford Balmoral

The Oxford is the most basic and timeless of the dress shoes, and a great starting point if you’re looking for a classic staple. They are a versatile option that can be dressed up with formal wear or down for a more casual arena. Gaining its name from its history at Oxford University, oxfords were a newer version of the popular Oxonians that were popular at the university circa 1800. This half-boot style was — at century’s turn – judged outdated, and students began looking for an alternative style. The oxford shoe was the fulfillment of longings for something modern.

The shoe is characterized by its facing being stitched under the vamp. This is called “closed lacing.” The facing’s placement provides a slim silhouette that hugs the foot’s contour.  It is on account of its minimalism (and ability to go with just about everything) that the Oxford enjoys its popularity. For general everyday wear, there are many colors from which to choose, in both leather and suede. For business attire, dark brown, cordovan, English tan, and black leather are your safest choices. If you’ll be pairing them with a tuxedo or other formal wear, black patent leather is your best bet.

The One Piece Oxford is a variation on the classic oxford, constructed of a single piece of leather rather than various pieces sewn together. This style has only one seam connecting the piece of leather to the back of the shoe while maintaining the original oxford shape and signature “closed lacing.” The limited stitching gives a sleek and sophisticated look that adds to the shoe’s simple, no-nonsense style.

Take the quiz: What shoes should you wear with your outfit? 

The Derby

The Ultimate Guide to Dress Shoes: Derby, Blucher

The Derby shoe, also known as the Gibson or the blucher, was originally intended as a sporting and hunting boot circa the 1850’s. At the turn of the 20th century, Derbies became accepted as appropriate footwear for the town. Derbies are often miscategorized as oxfords, as their shape is very similar and their differences are very slight. Though not obvious upon first glance, the difference lies in the placing of the face. The Derby shoe has the facing stitched on top of the vamp; with an oxford, tabs are sewn under the vamp. This construction, called “open lacing,” allows for a wider fit than is typical with an oxford. For many, this makes the Derby a more comfortable shoe. This simple detail has kept the derby reminiscent of its sporting roots, for which reason it is received as a less formal version of the Oxford.

Take the quiz: What shoes should you wear with your outfit? 

The Monk Strap

The Ultimate Guide to Dress Shoes: Monk Strap

A shoe with a monk strap is similar in shape and construction to an Oxford but in place of an eyelet closure, the monk strap has a wide swath of leather fastened across the front of the shoe. This is the “strap,” which is fastened with either a single or double-buckle closure. The shoe takes its name from the monks who originally donned them. The simple closed-toe design provided greater protection than the sandals traditionally worn by men in the orders.

How “formal” is a monk strap? All else being equal, the style itself lies somewhere between the Oxford and the derby. This classic alternative to laced dress shoes adds a certain panache to any outfit. While this has not always been the case, the monk strap is now regarded as a very versatile style of shoe style. It can be worn with cuffed jeans, or with the most dapper of suits. Monk strap attracts attention and may at times become the focal point of an ensemble. Monk strap shoes are often crafted out of leather or suede, and will sometimes decorative broguing.

Take the quiz: What shoes should you wear with your outfit? 

The Loafer

The Ultimate Guide to Dress Shoes: Loafer

The loafer is a moccasin-inspired shoe that is most recognizable for being a slip-on style. The loafer was originally intended as a casual house slipper made for King George VI of England. The loafer was neither acknowledged nor popular as a casual shoe until the King’s slippers crossed the pond. Manufacture of the loafer in the United States was underway in earnest by the 1930’s. It kept its status as a casual-only shoe until the 1960’s when American businessmen and lawyers began wearing loafers with suits. In 1966, Gucci introduced the bit loafer. This variant features a metal strap (in the shape of a horse’s bit) across the instep. Gucci’s innovation further elevated the loafer’s status as formal footwear — or at least confirmed that this was not strictly casual.

The loafer often features a saddle — a decoration that might be a plain strap, a strap with a slit (as with penny loafers), or a metal ornament. Tassels or a kiltie might hang from a saddle, while the minimalist version (the Venetian) has an exposed vamp absent embellishment or ornamentation. A signature characteristic of loafers (especially those nearer to a moccasin than a regal slipper) is an elevated seam that runs along the shoe’s toe. A very casual variant of the loafer is the driving moccasin or driving shoe. These are often made of softer materials, are less structured, and have soles and heels made to optimize wearer-comfort while driving.

Take the quiz: What shoes should you wear with your outfit? 

The Dress Boot

The Ultimate Guide to Dress Shoes: Dress Boot

dress boot is constructed like an oxford, and is very often the same shape, but with a longer shaft. This short, lace-up boot often features wingtip broguing on the toe and along its seams, typically rising over the ankle. This style traces its roots to the Victorian era when men’s footwear options were limited. The dress boot quickly became an accepted dress shoe option, appropriate for formal daywear. The place of the dress boot in menswear has remained much the same, and it is an attractive alternative to typical dress shoe styles.

When is a boot dressy enough?  It should be sleek, not too chunky, have laces thinner than those found on casual-wear boots, and should have soles which immediately distinguish the boot as a high-top dress shoe. Lug soles and commando soles will rarely be appropriate, though there are exceptions. If the boots are made of fine leather, their color doesn’t much matter so long as it compliments the suit. Unless you are an expert, assume that a suede dress boot is a contradiction (though it need not be).

Read: Essential Guide to Men’s Boots

The Chelsea Boot

The Ultimate Guide to Dress Shoes: Chelsea Boot

The Chelsea boot originated in Victorian England, reputedly with shoemaker J. Sparkes-Hall  (boot maker to the Queen Victoria). Then as now, the boots’ elastic gussets allowed for them to be pulled-on and slipped-off with ease, without compromising the refined silhouette of a laced boot. Indeed, the absence of laces contributed to their neat shape. The Chelsea boot became the practical alternative to the rigid Victorian boots of the age and quickly recommended themselves to the equestrian set. There was an uptick in sales the 1960’s when Mods took them from the paddocks to the pavements. Victorian naturalist Charles Darwin might have had a fondness for beetles, but The Beatles had a fondness for Chelsea boots. Thanks in part to blokes like them, the style remains popular today.

These boots are ankle length with rounded toes and low heels. The vamp and the quarters meet near the ankle and are joined by an elastic gusset. The Chelsea boot owes its clean, tidy look to the fact that – in dressier versions – the vamp and quarters are made from a single piece of leather. This keeps the stitching to a minimum. Classic Chelsea boots are absent decorative flourishes or embellishments. Their simplicity puts them in a class all their own: jeans get an upward lift, and traditional-style suits gain an edge.  If you purchase suede Chelsea boots, wear them only as part of a casual or smart-casual ensemble.

Take the quiz: What shoes should you wear with your outfit? 

The Chukka Boot

The Ultimate Guide to Dress Shoes: Chukka Boot

The Chukka has origins in the game of polo: it is the unit of time by which polo matches are measured. (A typical chukka is seven minutes long, and a polo match consists of four, six, or eight chukkas.)  Some have said that chukkas resemble shorter versions of the boots worn by polo players, but it is claimed also that they were intended to be a more comfortable version of polo boots that players could wear after the game — think the original Uggs and surfers.

Chukkas are ankle-length boots with two to three pairs of eyelets on each side for a lace-up closure. These eyelets allow for a snug fit around the ankle which, unlike regular boots, will not disrupt the shape of one’s trouser-bottoms. Chukka boots generally have a rounded toe, minimal stitching, and open lacing (similar to the derby). They are traditionally made of soft suede, but nowadays there are many versions from which to choose.

Chukkas are not to be confused with desert boots. Desert boots are a much more casual version of a Chukka boot and have a nearly identical shape. They are distinguished by soles that are not made of leather.

These are the least formal of the shoes we are discussing. They would not be appropriate for anything except casual attire, although pairs in high-quality leather compliment a smart-casual ensemble. Both chukkas and desert boots are exceptional.

Take the quiz: What shoes should you wear with your outfit? 

The Opera Pump

The Ultimate Guide to Dress Shoes: Opera Pump

Popular during the Victorian era, opera pumps were part of a formal evening wear ensemble. They are traditionally made of patent leather and are adorned with a grosgrain bow. Back in the day men would wear them with knee-high stockings and breeches to operas, dances, and other formal events. Though they are not as popular today, opera shoes will occasionally be seen at full-dress events, worn by fashion-conscious individuals.

Take the quiz: What shoes should you wear with your outfit? 

Dress Shoe Toe Styles

cap toe, wingtip, plain toe, medallion, apron, split toe

When making an investment in quality footwear, consider and take note of the details, because it’s all about details. As with everything relating to style, particularity about (and attention to) details enable you to bring elements of personality to your ensemble. When choosing your next pair of dress shoes, abide by the one golden rule: the toes of your shoes should be rounded, and never squared or pointy. There’s a time and place for this style of toe but we are now discussing investment in a pair of dress shoes.

Plain Toe

Plain toe shoes are as simple as it gets. The vamp is unadorned. The resulting look is clean and unassuming.

Cap Toe

A cap toe has a horizontally stitched line across the vamp of a shoe — it “caps” the toe. In most cases, this will actually be a separate piece stitched as the toe on the vamp, but sometimes the cap is accomplished by stitching. Many cap-toe shoes will be in the Oxford style, but the cap can appear on other styles too.

Split/Apron Toe

The split toe, otherwise known as the apron toe, features a seam that begins in the middle of the shoe, runs around the toe, and ends at the middle of the shoe on the other side. This toe style is more common in casual shoes.


The medallion style has a plain toe and hints of brogue decoration at the toe.


This toe style has a winged cap that peaks in the middle of the toe. This toe style often features broguing in the center of the toe and along the seam of the cap.


Any dress shoe style can have brogueing. Brogue simply refers to the decorative perforations in various patterns on dress shoes. Originally, the perforations were holes which were intended to allow water out of shoes: when yomping across crossing wet terrain (wet shoes being inevitable), the holes let water be squeezed out with each step. Brogueing is most often seen on Oxford, derby, and monk strap shoes, and is available in four different toe cap styles: full brogue, longwing brogue, semi-brogue, and quarter brogue.

full brogue, semi-brogue, half brogue, quarter brogue, longwing, long wing brogue

Full Brogues / Wingtips

Also known as wingtips, the wing-shaped cap extends around to the outside of the toes.

Longwing Brogues

Longwing brogues are most commonly seen on the derby shoe. The shoe’s brogued wingtip cap continues along the side of the shoe all the way to its center seam in the back.


Semi-brogues, also known as a half brogues, feature broguing along the seam of the cap toe as well as some decorative broguing on the center of the cap toe. This is more subtle than a full brogue.

Quarter Brogues

The most reserved of the lot, the quarter brogue simply features decorative broguing along the seam of the cap toe, with no decoration on the center of the cap toe.

Take Your Pick

A signature pair of well-made dress shoes is an essential possession. Choose a well-crafted pair, and choose wisely. Ideally, your selection will express your personal style, and “fit” with the ensembles you are most likely to be wearing. You can add a little more dimension to your dress shoes through creative lacing or the addition of a colorful laces. Not every man will be able to spend a fortune on dress shoes. As you consider your budget, we recommend taking into consideration how often you will be wearing them, and where you will be most likely to be wearing them. If use is likely to be limited mainly to the occasional wedding, funeral, etc., there’s no need to break the bank. If you are most likely to be wearing your dress shoes as part of your business/professional ensemble, spend a bit more than you’d like to. If you will be wearing them regularly, we recommend spending as much as you can comfortably afford to spend, and that you consider a well-made pair of dress shoes a small investment.

Take the quiz: What shoes should you wear with your outfit? 

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The Ultimate Guide to Dress Shoes

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body geometry – wear your size

Gentleman’s Geometry: Dressing for Your Body ShapeFind your fit and embrace your size 

Written by Meghan Salgado

If you’re searching for a guaranteed way to look put together (or trying to avoid looking like you don’t know what you’re doing) attention to the fit of your clothes is essential. Anything that’s too large for your frame looks sloppy, while clothing that’s too tight may accentuate body parts that don’t need attention. While the principle of fit is simple to understand, carrying it out can be a little bit trickier. We’ve laid out some basic profiles to help you understand what your body type is and what will look best on your frame. 



This is you if:

You have a pretty average build. Your chest and waist are well-balanced, and your shoulders are only slightly wider than your midsection, giving your upper body a slight taper. You might work out for a little definition but you don’t have that gym rat build (see below). Your legs are also balanced with your upper body. You’re in luck because this is the body shape most menswear brands cater towards. The way clothes look online will most likely be similar to how they’ll look on you. You have the freedom to try riskier prints and proportions. Use that to your advantage to build a more distinct and adventurous look.

What to Wear


On the Daily

  • Slim fit trousers: You don’t need to use extra fabric or extreme tailoring to change your silhouette. Instead, emphasize your natural shape with close fitting pants. Since your shape is industry standard, you should be able to buy pants marked “slim fit” off that rack and have them look like they were made for you. 
  • Patterns: Don’t shy away from something a little bit louder because you have the body shape to pull it off. This isn’t an excuse to throw on your best Hawaiian shirt, but you can go bold. Try a strong geo print in a bright color. 
  • Standard ties: Since you’re so well balanced, anything other than a standard size tie looks a little wonky on you. Skinny ties will make you look too broad and anything extra long could make you look short. If you really need something a little different, go with a bowtie. 

In a Suit

  • Well-tailored trousers: Same rules as your everyday look, make sure your pants skim your body and have a slimmer fit. Ask your tailor for a slight break or no break (where your pant leg hits your shoe), as this looks best with slim fit trousers and will give you a contemporary, modern look.  
  • Taper at your waist: Make sure your jacket comes in at the waist to avoid an unbalanced look between your top and bottom half. Even though your frame leaves some room for mistakes, it’s also easy to get a good fit. Your body type makes it easy to find the right jacket without any tailoring, so hold out for the right piece.



This is you if:

You’re straight through the torso with shoulders that are the same width as your waist, and you may have been called “beanpole” at some point in your life. Your skinny top half is matched by equally slim legs. Your above average height makes fit a bit of a challenge when you find yourself trying to match the length and width of your clothing. Wide fits leave you with a boxy silhouette and large patterns make it look as if you’re being swallowed up by fabric, so avoid both of these. Layers and heavy fabrics are your friends as they create the illusion of a heavier frame, especially on your top half.

What to Wear


On the Daily

  • Layers: Knits, cardigans, or jackets are all great for adding some weight to your shoulders to create the illusion of a trapezoid build. Heavier fabrics, in general, will draw the eye upward and put more bulk on your frame. 
  • Details across shoulders: Perfect for summer when the last thing you want to do is put on another layer. Color or detailing on the top half of your shirt will create the same effect as layers with a little less heat. Try to draw the eye upward and accentuate your shoulders to create a broader look. 
  • Slim fit trouser: A close fit in your trousers will also help you keep your proportions in check. Anything wider won’t add bulk but actually, makes you look skinnier as the excess fabric overwhelms your frame.

In a Suit

  • Pant Length: The shortest you should ever go on your pant length is the no break look. While the cropped look may be fashion forward, it throws off the balance between your top and bottom half 
  • Single breasted jackets: Single-breasted jackets are a must for your frame, as a double-breasted look will make you look even more rectangular. Some structure in your shoulders is also ideal to fill out your top half.

Inverted Triangle


This is you if:

Sometimes you have trouble walking through door frames. Okay, your proportions may not be that extreme but your shoulders are definitely the widest part of your body and are accompanied by a more tapered waist than someone with a trapezoid build. Since you (hopefully) haven’t been skipping leg day, you may also have some bulk in your thighs, giving some visual weight to the bottom half of your body as well. This can be a difficult body to dress, with most retailers catering bodies less fine-tuned than yours. Luckily, the athleisure trend gives you some room to breathe and the chance to wear something other than sweat-wicking shirts.

What to Wear


On the Daily

  • Straight-leg trousers: Add some balance on the bottom with a straight line in your pant leg. A little more fabric here will add to your frame and keep your pants fitting comfortably. 
  • Horizontal stripes: Your waist is by far the smallest point of your body. A bold stripe can help widen you in the place that you need it most and draw attention away from your broad shoulders.  
  • Belts: Another tactic for drawing the eye a little lower is adding a belt to your getup. Whether you’re wearing shorts or full-length pants, adding one in a standout color will break up your frame a little.  

In a Suit

  • Small to medium patterns: Since your build is bigger, keep the patterns you’re wearing smaller to downplay your size. Small polka dots or more intricate patterns on your shirt will look best on you. 
  • Tailor the waist: You’ll certainly need extra room in the shoulders, so opt for a size up in your suit jacket and plan for your tailor to take it in at the waist. A boxy, unfitted look isn’t flattering on anyone. Despite your slender middle, your jacket should still taper in.



This is you if: Your midsection is wider than your shoulders This build becomes more common post-college, but does not mean you’re out of shape. Some people’s bodies are more inclined to this build than others. Your legs also have some shape to them and are balanced out by the top half of your body. The most important thing to be wary of is the pinch from trying to dress for the slimness of your shoulders that could cause some tightness around the belly. Looks that work for you (particularly on top) overlap with what looks good on the rectangle-shaped man.

What to Wear:


On the Daily

  • Structured shoulders: Since your midsection is the widest part of your body, structured shoulders are perfect for balancing it out. This will minimize the visual appearance of any weight on your waist and make you appear more proportional. 
  • Detailing/color across your chest: Again, anything that will draw the eyes upwards to your shoulders is a good look for you. Color and detailing that brings the eyes up to your chest is a more flattering look on you. 
  • Straight leg pants: When it comes to pants, taper at your own risk. Anything too slim fitting will draw attention straight to the largest part of your body. A straight legged look, and even some pleats, will give you more balanced look with some extra comfort.  

In a Suit

  • Single breasted jacket: The volume of a double-breasted jacket will bring too much weight to your top half. Instead, invest in a classic single-breasted jacket that will sit close to your frame. Structured shoulders will draw the eyes up and balance out your middle with this more formal piece. 
  • Darker dress shirt: A darker, deeper color could be more flattering than your standard white dress shirt. The tone will look slimming on your larger top half and create a nice monochrome look with the rest of your suit.

re-invent your style

How to Reinvent Your Style An unbeatable guide for starting over

Written by Salvatore Marashi

Stagnation is the gravest enemy to a great man. Likewise, your style needs to be invigorated periodically. It’s a new year, Gentlemen. Why not do a little reinventing?

We’re not big on simply chasing trends here, but sometimes wearing the same thing day in and out can make us feel, well, tired. It’s funny how changes in appearance affect how you feel about yourself.

Here’s our primer on reinventing your style for the better.

Reinventing Your Style

Out with the Old

reinventing your style out with the old

Unsplash Crew

There’s a lot of junk in your closet. How many tee-shirts did you forget that you even had? Before you can start reinventing your style, you need to get rid of all the stuff that put you in this rut in the first place.

Identify these clothes and be brutal with your purging. Keep only things with sentimental value (which, doesn’t mean you have to wear it), or essential pieces like basics that can be incorporated into your new look. Out with the old so you can make way for the new.

Finding Inspiration

reinventing your style finding inspiration

So you’re seeking change, but you don’t exactly know what you want it look like. Finding inspiration is easier than ever. With Instagram, celebrity style icons, and great fashion sites (like ours), there are plenty of places to look.

Instead of imagining your clothes, first picture how you want your new style to make you feel.

With that in mind, seek out other guys with that air about them. What are they wearing?

Before settling on a decision, consider your lifestyle. You might want to wear Hawaiian shirts every day, but is your boss going to like that? Just because you’d like to look a certain way doesn’t mean your environment will support it. Although there’s plenty we all wish we could change about the world, I’m sure.

Think of it as reshaping your style, so you can try something new without breaking the confines of what’s reasonable.

Start Small

reinventing your style start small

Before throwing all your old clothes in a burning pile and dancing to their destruction (or if you’re boring, donating them), test the waters. Start small by experimenting with subtle changes. A new pair of sunglasses or picking up some men’s jewelry might give you what you’re looking for.

Build Up

reinventing your style build up

Changing your style begs for an understanding of what the new one will be. This is a process. While you’re becoming an expert in your new look, it’s wise to build up. Start with the basic pieces of that style. Think of changes like a neon watch strap or camo sneakers.

These simple additions provide a solid base from which to expand, while still being easy to incorporate into your current wardrobe.

Invest Wisely

reinventing your style invest wiseley


Reinventing your style can be a costly affair. Budget and pace yourself. Poor spending habits may have led to your current wardrobe fatigue.

Instead of buying anything in the realm of your new style, be selective. Thoughtfully choose items that will work together.

Cohesion in your wardrobe will maximize every piece in it, ultimately making the most out of your money. A couple of synergistic pieces are always better than a host of mixed-matched ones.

Budgeting is especially crucial if you’re upgrading to a more expensive look. Save where you can on basics, and invest in the statement items. Meaning, opt for cheaper t-shirts and occasionally splurge on a quality blazer or jacket. Your new style will depend more on these big pieces.

Time to be Bold

reinvent your style time to be bold


Once you have a grasp on your new style, it’s time to be bold. Playing it safe with your sartorial reinvention is defeating the purpose. Get out of your comfort zone and get noticed.

Play it too safe, and you’ll be bored again in no time. Fashion is meant to be a fun method for self-expression, so get creative with it.

Consider a Different Brand

reinventing your style consider a different brand

David Lezcano

Whether we mean to or not, we often gravitate toward the same stores over and over again. It makes sense. If that store had one thing you liked, chances are you’ll find something else there that fits your aesthetic.

That’s great when you’re happy with your wardrobe, but it’s a problem when you want to branch out. Finding another brand can give you a litany of new style options. Diversifying where you shop is crucial to keeping things fresh.

If you’re in need of some examples, check out the comprehensive list of our favorite places to shop, here.

Beyond the Clothes

Reinventing your style doesn’t have to be limited to clothes. Here are some ways you can reinvent yourself beyond textiles.

Choose a New Hair Style

reinventing your style choose a new hair style

Firza Pratama

Most guys pick a hairstyle as a kid or teen and stick to that pretty much their whole lives. If that’s you, you’re missing out. There are tons of men’s hairstyles, from slick-backs to buzzcuts, to a dozen varied types of fades.

When choosing a hairstyle, factor in how it plays with the rest of your reinvented style. For instance, if you’re going for an edgy IDGAF look, you can consider a faux hawk. But if you’re aiming for something more professional, you can’t go wrong with a quiff.

Take the discovery quiz: Find Your Perfect Haircut

That best part about reinventing your style through hair is that it grows back. So if you didn’t like it, you could start over in a few months.

Changing your Grooming Game

reinventing your style grooming

Drew Hays

Another super easy way to reinvent your style is through grooming. If you’ve just been clean shaving, growing out a Van Dyke or sporting a Chevron mustache can completely change things up. On the flip side, if you’ve had a beard so long that you can’t remember what your face looked like without one, maybe it’s time to revisit your baby-faced days and go clean-shaven.

Don’t forget to build a grooming routine that you can stick to.

A New Body Through Exercise

reinventing your style new workout

I. Yunmai

Your body is the outfit you can’t take off. Improving your physique will massively change your look, of course. The shape you’re in correlates directly to how your clothes fit.

While maintaining a healthy routine, you might find that those clothes you were ready to get rid of? They’re now exactly what you wanted in the first place.

Go get Started

Reinventing your style is daunting but there’s no better time to start than the present. With these tips in mind, building a better look is easier than ever.

Some 2019 Trends

We’ve curated from high to everyday-brow. Again, we’re not particularly keen on fleeting trends, but it’s cool to know what’s out there. Here are some possible inspirations for your journey:

According to Pinterest trends, here’s the latest in men’s fashion based on image searches:

  • Vintage wrist watches (Searches for vintage watches +98%)
  • Light-wash denim (Searches for light washed denim +70%)
  • Sling-bags (Searches for sling bags +1184%)
  • Corduroy (Searches for corduroy +507%)
  • Mismatched patterns (Searches for mismatched prints +89%)
  • Fades for hair (Searches for french crop haircuts +84%)
  • Plaid (Searches for plaid pants +267%)
  • Men’s scarves (Searches for neck scarves +29%)
  • Cropped trousers (Searches for cropped trousers +671%)
  • Quarter socks (Searches for quarter socks +266%)

And if you’re of the bourgeois persuasion, here’s what Vogue has to say by observing fashion-forward gentlefolk in metropolitan areas:

  • Cross-body bags
  • Animal print
  • Long and luxurious coats
  • Leather jackets
  • Puffy jackets
  • Casual, oversized suits
  • Wide-legged pants
  • Workwear and utility jackets
  • Berets
  • Men’s scarves

shop online here


Essential Guide to Men’s BootsFrom Chelseas to Jodhpurs to Workwear

Written by Janet Hu

[Feature Image by Articles of Style]

Pretty much every guy can rock sneakers. And most men own a pair of dress shoes. Boots, however, are a heavily underutilized form of footwear, and we think it’s because not many people know where to start. That’s a shame, since men’s boots come in such a wonderful range of designs, heights, materials, etc.

In this essential guide, we’re outlining the different types of men’s boots and giving some pointers on how and when to wear them:

Men’s Boots: Chelsea Boot

men's boots cheslea boots

Thursday Boot Company

Height: Ankle

Laces or Pull-on: Pull-on

Style: These close-fitting boots have an elastic side panel, and they are typically made of suede. Men and women first wore Chelsea boots in the 1800s Victorian era. Then in the ’60s, these boots made a re-emergence in British mod fashion when they became the Beatles’ footwear of choice.

men's boots chelsea boots

The Idle Man

How to wear it: The Chelsea boot is semi-casual but trendy. Wear them with dark jeans and a blazer, sports coat, or leather jacket.

Men’s Boots: Cap Toe Boot

men's boots cap toe boot

Cole Haan

Height: Ankle

Laces or Pull-on: Laces

Style: Cap toe boots feature a straight-seamed cap over the toes. These leather boots are considered more formal and can be worn with dress slacks, chinos, nice jeans, and blazers.

men's boots cap toe boots

J. Crew

How to wear it: You can wear cap toe boots with a winter suit and overcoat. Think: swank Sherlock Holmes.

Men’s Boots: Wingtip Boot

men's boots wingtip boot


Height: Ankle

Laces or Pull-on: Laces

Style: These low-heeled leather boots are similar in style to cap toe boots. Instead of a straight seam across the toes, though, wingtips feature a “W” shaped cap that extends toward the heel. Wingtip boots have decorative perforations along the seams. Originally called “brogue shoes,” wingtips used to be considered a strong outdoor shoe, made from untanned leather. They’re now often worn in offices, though still considered more casual than cap toe boot shoes.

men's boots wingtip boots


How to wear it: Wingtip boots are semi-formal. You can wear them with a flannel suit or with dark jeans, a collared shirt, and a sweater.

Men’s Boots: Desert Boot

men's boots desert boots

Kenneth Cole

Height: Ankle

Laces or Pull-on: Laces

Style: These boots originated in the ’50s as combat footwear worn by British soldiers in WWII. They feature fewer eyelets than the average lace-up boot, making them easier to slip on and off. Now, desert boots are often made of tanned leather or suede, and they typically have crepe soles, which are soles made of latex and rubber. These boots exist in the territory between formalwear and combat, and they are signature to rogue style stars like legend Steve McQueen.

Desert boots are a type of Chukka boot. The Chukka style is any ankle-high boot with a low number of eyelets.

men's boots desert boots

East Dane

How to wear it: Desert boots are part of your “likes artisan beer” and “hipster variety.” Wear them with a pair of nice, rolled pants.

Men’s Boots: Jodhpur Boot

men's boots jodhpur boots


Height: Ankle

Laces or Pull-on: Pull-on

Style: This is an ankle-length riding boot with a rounded toe and low heel. The Jodhpur boot’s straps are a defining characteristic. They attach to the vamp and can be fastened with a buckle. These boots originated in India during the ’20s and were worn by local polo riders. Then in 1927, Saks Fifth Avenue began selling these boots as fashion wear in the West. Vogue once wrote that Jodphur boots should be worn with a swagger stick and canary string gloves.

men's boots jodhpur boots

Thursday Boot Company

How to wear it: Jodhpur boots are considered dressy, though not exactly formal. They’re a little exotic and ornate. Wear them with a trendy blazer or cool leather jacket.

Men’s Boots: Riding Boot

men's boots riding boot


Height: Knee

Laces or Pull-on: Pull-on

Style: Riding boots come up to the knee, and they are often made of patent, or shiny, leather. These boots are for dressage, formal fox hunting, and show jumping. Tall boots once protected riders’ legs from the saddle. That is, until Jodhpur riding pants with baggy thighs came along, and ankle Jodhpur boots became the new riding boot.

men's boot riding boot

Massimo Dutti

How to wear it: We’re going to be honest: this is not an easy one to pull off. But the image above is a good example of how you can dress down an otherwise very noticeable boot. Wear riding boots with a collared shirt or blazer and some chinos.

Men’s Boot: Harness or Motorcycle Boot

men's boots motorcycle boots

Extreme Biker Wear

Height: High-Ankle to Mid-Calf

Laces or Pull-on: Pull-on

Style: These boots made of thick, heavy leather protect motorcycle riders from exhaust pipes and engine heat. They have a low heel and unadjustable straps closed with metal rings. Harness boots will sometimes include a built-in steel toe cap and metal shank in the heel to protect riders from injury.

men's boots harness boots


How to wear it: Harness boots have an alternative and dark aesthetic. That’s why characters from The Vampire Diaries would be sporting them. If you’re looking to add a heavy-duty or metal edge to your look, wear harness boots with dark colored clothing. You can also opt for brown boots instead of black, for a less intense look.

Men’s Boot: Cowboy Boot

men's boots cowboy boots

El Presidente

Height: Mid-Calf

Laces or Pull-on: Pull-on

Style: These boots, typically made from cowhide, have a low heel and a rounded or pointed toe. They are often decorated with ornate top-stitching or geometric cutouts and have an under-sling heel–that is, a heel that curves inward. As the name suggests, these boots were originally worn by American cattle ranchers in the 1860s. Some cowboys wanted nicer boots to wear into town and thus came the ornate designs. Today, some cowboy boots are even made of exotic alligator, snake, or eel skin.

men's boots cowboy boots


How to wear it: Wearing cowboy boots with anything but denim would be almost sacrilegious. Keep your look casual and rugged. Wear a loose-fit collared shirt, maybe even a Western-style button down, to pull off the country rustic aesthetic.

Men’s Boot: Workwear Boot

men's boots workwear boots

Red Wing

Height: Ankle

Laces or Pull-on: Laces

Style: Workwear boots have thick, water-resistant material and rubber soles. They have a chunkier, sturdier look. Originally intended to protect workers from chemical substances and water, snow or mud, workwear boots are perfect for hiking. These boots also became fashion staples in hip-hop and punk scenes with popular brands like Doc Martens and Timberlands.

Actual safety boots may feature a steel cap over the toe to protect wearers from debris-related injury.

men's boots workwear boots

Blue Collar Prep

How to wear it: Workwear is at the intersection of street, grunge, and trendy. You can pair workwear boots with light denim and a long overcoat, Kanye style.

Looking forward to your new sartorial adventures. Which boot style would you try first? Let us know in the comments.

do check our latest styles here.