Collection of mens boots

Essential Guide to Men’s Boots From Chelseas to Jodhpurs to Workwear

[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.

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

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:

Table of Contents

Men’s Boots: Chelsea Boot

men's boots cheslea boots
Thursday Boot Company

Bruno Marc Men’s Suede Leather Chelsea Ankle Boots

Stretch bands with good elasticity and pull up tab for easy on and off

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

Eastland Men’s Jayce Cap Toe Rugged Boot

  • Rubber sole
  • Unlined, full-grain leather upper
  • Removable, soft, breathable fabric-lined insole

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

Johnston & Murphy Men’s XC Flex Cody Wingtip Zip Boot

  • Sheepskin/moisture-wicking textile lining.
  • Removable EVA insole with memory-foam cushioning.
  • Inside zipper for on/off ease.

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

Bruno Marc Men’s Classic Suede Leather Desert Chukka Boots

  • 100% Suede Leather
  • Suede sole
  • Shaft measures approximately 4 from arch

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

Frye Men’s Grady Jodphur Chelsea Boot

Shaft measures approximately ankle-high from arch

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

RIDETECS 16″ Leather Biker Riding Boots For Men, Black – Tall & Wide Calf Adjustable Vamp With Side Ankle Straps

  • 100% Heavy Duty Full-Grain Oiled Leather
  • Boot opening measures approximately 10 around
  • Split Shaft, Adjustable Vamp & Ankle Straps

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

Xelement 1502 Men’s ‘Killa’ Black Leather Zippered Harness Motorcycle Boots – 10.5

Made of Black Heavy Duty Full-Grain, Oil Tanned Leather Upper

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

Canyon Trails Mens Classic Durable Round Toe Embroidered Western Rodeo Cowboy Boots

  • Rubber sole
  • Shaft measures approximately Calf High” from arch
  • 100% original high quality.

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

Irish Setter Men’s 6″ 83605 Work Boot

Irish Setter has developed outsoles that have been designed and tested to perform on high heat surfaces. 

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.

Read Workwear Style: How to Wear It

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.

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

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