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.

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How to lace all your dress shoes(the right way)

…don’t let your formal look down with your last detail…

Even that three-piece Tom Ford suit isn’t going to be enough to make you look good when you’re lying face down in a pile of your own teeth, surrounded by startled party guests, with your shoes a few yards behind you.

While it may be an unpleasant one, that mental image should illustrate to you the importance of ensuring your smart footwear is laced up correctly.

We know, tying your shoes isn’t exactly rocket science. After all, the likelihood is you’ve been able to do it since before you could even spell shoelaces. However, not all footwear was created equal and different smart shoes require varying lacing methods.

What Are Smart Shoes?

It may sound obvious, but every weekend thousands of men are left scratching their heads after being turned away from nightclubs for wearing their Nike Air Max. This suggests that there is still some confusion about what the term ‘smart shoes’ actually means. So, let’s revisit the basics for their sake.

Being as broad as possible, if you’d wear it to the office with a suit, chances are you can consider it a smart shoe. We’re talking leather, black or brown, no excessive detailing and certainly no big logos.

Closed Lacing Vs. Open Lacing

When it comes to lacing your smart shoes, you’ll need to understand the subtle difference between what are referred to as closed-lace and open-lace styles.

In closed-lace styles, the part of the shoe that covers the front portion and sides of the foot, known as the ‘vamp’, is stitched over the bottom of the part of the shoe that contains the eyelets, known as the ‘facing’. This results in a cleaner overall look but at the cost of flexibility. In general, closed-lace styles tend to be much more formal due to their uncluttered appearance.

Open-lace styles differ in that the facing is stitched on top of the vamp. This offers more room for adjustment and makes shoes more flexible, but it’s not seen as ‘dress shoe’ styling owing to the busy look this creates on the upper.

What Is An Oxford Shoe?

Weirdly enough, Oxford shoes first appeared in Scotland and Ireland. They feature a closed lacing system and have become the definitive dress shoe and the only real choice when it comes to black-tie dress codes.

However, the Oxford isn’t exclusively a dress shoe. Added detailing such as wingtip panels and perforated patterning known as ‘broguing’ can help to make the style look a little more laid back.

Because of this, the Oxford is the only shoe that can function with everything from a tuxedo to a pair of jeans and a T-shirt.

Oxford Shoe Closed Lacing System

What Is A Derby Shoe?

The Derby shoe is a businessman’s best friend. The trusty stomper that’s comfortable enough to be worn every day, yet smart enough to do a suit justice. It may not be as dressy as an Oxford, but hey, it never claimed to be and what it does do, it does well.

Unlike its Oxford cousin, the Derby features an open lacing system. The facing on a pair of Derbies is always open at both the top and the bottom, which is the reason for their trademark comfort.

For an everyday shoe that can hold its own in the boardroom, a Derby is what you need.

Derby Shoe Open Lacing System

How To Lace Oxford Shoes

Due to their closed lacing system, Oxfords have to be laced up in a certain way. If you’re replacing the laces in your shoes, measure your old ones to ensure you get the best possible fit. Then it’s a case of finding something thin and round that matches the colour of your shoes perfectly. There’s no room for colourful statements here.

Once you have the right laces at your disposal, you’ll want to use one of two methods: either European straight lacing or ladder lacing. Both of these methods will leave you with neat horizontal lines running from eyelet to eyelet, while the lacing hidden underneath will allow you to tighten things up.

“Ladder lacing, or show lacing as it sometimes called, is only really practical on shoes with less than four eyelets,” explains Oliver Sweeney’s cobbler-in-chief Tim Cooper. “This is as it doesn’t pull evenly and over time will pull the shoe out of shape.” European straight lacing is more versatile, so if your pair has more than four eyelets, go for this method.

Steps for European Straight Lacing Smart Shoes

Steps For European Straight Lacing

  • Insert both lace ends downwards into each of the bottom holes.
  • Take the left lace and insert it up and through the next free right eyelet.
  • Take the right lace and place it up and through the third eyelet on the left, skipping out the second. There should now be an empty hole on the left hand side.
  • Insert what is now the right lace downward into this free eyelet, which should be directly opposite it.
  • Follow this process until completion, repeating the steps above for each lace.

How To Lace Derby Shoes

The process for lacing a pair of Derby shoes is much the same as the process for lacing a pair of Oxfords. First, you’ll need to find laces that are the correct length, colour and shape to fit your shoes, then it’s a case of fixing them in place.

Again, these are smart shoes so the method of lacing should be neat. However, the difference here is the open lacing system which means the tongue of the shoe tends to be partly visible. This rules out any type of lacing that uses diagonal lines to tighten the shoe, so the best option is to use straight bar lacing, which snakes in an ‘S’ shape from eyelet to eyelet, leaving straight lines with everything else hidden beneath the facing.

Steps For Straight Bar Lacing Smart Shoes

Steps For Straight Bar Lacing

  • Insert both lace ends downwards through the bottom two holes, leaving equal length on both the left and right laces.
  • Looking down on the shoe, insert the left lace up and through the next right hand hole, with its end pointing to the ceiling.
  • Now put the right lace up and through the third eyelet on the left, skipping out the second. There should now be an empty hole on the left hand side.
  • Take what is now the right lace and cross it over, inserting it downward through the empty eyelet on the left. This should create another straight bar, mirroring the first.
  • Do exactly the same with the left hand lace and cross it over, inserting it downward through the empty eyelet opposite it. You should now have three bars.
  • Keep lacing in this way, crossing each lace over to its opposite side to make new bars until you reach the top.