Probably the most popular boot style out there, Chukka boots are extremely versatile. Often associated with derbies and Chelsea boots, they’re almost identical to desert boots. However, despite their versatility, they can be challenging to wear properly.

In this guide, you’ll learn about Chukka boots as we cover the following points:

Scroll down to read the full guide or use the links above to jump ahead!

Johnston & Murphy Chukka Boots

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Quick Buyer’s Guide

Just looking to pick up a pair of Chukka boots? Use the Quick Buy guide below to head straight to the retailers. Otherwise, scroll down to read our full guide!

Clark’s

Clark's Blue Nubuck Chukka Boot

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Wolf & Shepherd

Wolf & Shepherd Striker Chukka Boot

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Clark’s

Clarks Casual Desert Boot

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Johnston & Murphy

johnston & murphy forrester chukka boot

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Carlos Santana

CARLOS by Carlos Santana Corazon Chukka Boot

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Dr Martens

Dr Martens Cabrillo Chukka Boot

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What Are The Best Chukka Boots For Men?

This section of our guide will help you find the best Chukka boots that offer the most bang for your buck. You can use the following menu to quickly jump between each shoe or scroll down to discover them all!

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1. Clark’s Atticus Limit [Best Value]

Clark's Blue Nubuck Chukka Boot
  • Color: Black, Navy, Taupe, Tan
  • Material: Nubuck Leather
  • Pricing: $125 [Buy On Amazon]
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As part of Clark’s Artisan Collection, the Atticus Limit represents the brand’s heritage. Famed for their desert boots listed below, their Chukkas feature all the traditional hallmarks of the shoe style. However, the Nubuck uppers conceal an OrthoLite footbed and comfortable rubber sole.

2. Wolf & Shepherd Striker [Most Comfortable]

Wolf & Shepherd Striker Chukka Boot
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Available in a pebble leather “bullet” tan, chocolate suede, or black full-grain calfskin, these are probably the most comfortable chukkas you could own. Rather than crepe, the soles are made from the brand’s lightweight PhoenixTech rubber while the footbed features memory foam.

3. Clarks Desert Boot [Alternative Chukka]

Clarks Casual Desert Boot
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Although technically not a chukka boot, the dessert boot shares many features. In fact, they’re indistinguishable to the untrained eye! Inspired by the boots worn by British officers during the Second World war, these are very style boots for casual wear.

4. Johnston & Murphy Copeland [For Winter]

johnston & murphy forrester chukka boot
  • Color: Black, Brown, Tan
  • Material: Leather
  • Pricing: $160 [Buy From Zappos]
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Aside from the Wolf & Shepherd chukkas, which are quite exceptional, the Copelands by Johnston & Murphy are somewhat premium for the style. Lined with sheepskin, they’re very comfortable to wear and very warm indeed!

5. Carlos Santana Corazón [Most Stylish]

CARLOS by Carlos Santana Corazon Chukka Boot
  • Colors: Black, Brown
  • Material: Full-Grain Leather
  • Pricing: $140 [Buy Now On Zappos]
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A stylish reinterpretation of the chukka boot, the sleek Corazón by Carlos Santana is more than a cash-in on the legendary guitarist’s name. They’re made from rich full-grain leather with a Blake stitch construction. Furthermore, they’re available in both black and brown in either full-grain or suede leather.

6. Dr Martens Cabrillo [Most Affordable]

Dr Martens Cabrillo Chukka Boot
  • Colors: Black, Brown
  • Material: Wyoming or Virginia leather
  • Pricing: $80 [Buy From Zappos]
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Available in either brown Virginia or black Wyoming leather, the Dr Martens is an affordable chukka boot that offers some excellent value for money. It’s a stylish blend of Dr Marten’s ruggedness and iconic soles with the chukka boots rustic aesthetic.

What Are Chukka Boots?

Top And Side View Of Brown Chukka BootsA chukka boot is an ankle-height lace-up boot, typically with only two eyelets.

A well-stocked gentleman’s shoe collection contains more than just black lace-ups, brown loafers, and gym shoes.

You don’t need a collection in the triple digits, but you should have some options at your disposal for any occasion you can think of.

Though boot season is technically comes and goes worldwide, it makes sense to talk about a classic boot that can be dressed up or down depending on its make and the outfit with which you pair it: the chukka boot.

History Of The Chukka Boot: Colonial India

Like madras and seersucker, the chukka boot comes to us from India via the British Raj, which wielded power in India from 1858-1947. Its name is taken from polo, as “chukka” or “chukker” is used to refer to a period of play during the game.

They are made in dressy calfskin versions with leather soles, casual suede with rubber soles, and even in sneaker versions (think high-tops). Plenty of companies make them ready-to-wear, and of course any custom shoe maker can create a pair to your exact specifications.

It’s sometimes referred to as a “turf” boot, though this is rare compared to the ubiquitous word “chukka.” Desert boots are a specific version of the chukka.

Nowadays, chukkas can be found with more than two eyelets in innumerable colors and materials. Their defining factors are being ankle-height and taking laces.

How To Style Chukka Boots

Formality: Can You Wear Chukkas With A Suit?

Trevor Guilday On Railroad With Leather Chukka BootsThere are no hard and fast rules when it comes to wearing chukka boots, but they tend to go best with flannels, corduroys, and jeans.

They can be worn with suits in colder weather. To do this well, your boots must have a proper dress sole and heel, and it’s advisable that the upper be made of black or brown leather as opposed to suede. It would make sense for such a pair to be waterproof so as to be helpful during inclement weather and perhaps negate the need for overshoes.

Here are a few different styles of chukka boot and some suggestions for clothing pairings:

  • Sneaker: Light denim, very casual khaki pants (note that this is a chukka boot with no dress sole or heel rather than a high-top sneaker)
  • Suede: Slim dark denim, cords, flannel or twill trousers
  • Leather: Dark denim, flannel trousers, worsted or flannel suiting

Brown Chukka Boot With Tan Laces

Seasonality: When Can I Wear These?

Being a boot, it’s best to wear them only in autumn or winter. Boots in spring and summer aren’t practical and will make you look like you’re trying too hard. It’s kind of like wearing sunglasses indoors: affected and silly.

An exception to this would be if you are wearing desert boots in early spring or if you live in a climate that’s cool enough year-round to warrant wearing boots anytime.

  • Spring: Unless they’re desert boots, no.
  • Summer: N/A
  • Autumn: Suede in any shade of brown or pebbled leather for day, smooth brown or burgundy leather for night
  • Winter: Dark leathers like black or brown, possibly with a rubber sole for days with lingering snow on the ground

A Final Thought

Lacing Up Johnston & Murphy Chukka Boots

As a presumably aspiring well-dressed man, it behoves you to own at least one pair of chukka boots. On the dressy end, they’re a great alternative to oxfords or derbies. More casually, they can be worn in place of a casual blucher or sneaker.

We advise that a chukka boot be perhaps the fifth or sixth shoe you pick up to round out a collection of classics. Oxfords, bluchers, loafers, and monk straps should theoretically come first. However, if it’s getting cold and you’re looking to get a pair anyway, treat yourself. If you invest wisely, you’ll get years of stylish comfort out of them.

What Next?

Now that you have learned about chukka boots, check out some our related footwear guides for men:

Men's Chukka Boot Guide
Reviewed by Theo D., on .
"A superb piece! Thanks for this, it helped me pick out some nice Chukkas and plan how to accommodate them into my wardrobe."
Rating: 5.0 ★★★★★

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