Top And Side View Of Brown Chukka BootsA chukka boot is any 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.

What Is A Chukka Boot - Bespoke Unit

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How To Style Chukka Boots

Formality: Can You Wear Chukkas With A Suit?

There 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

Top Chukka Boot Makers

While you can buy chukka boots from nearly any footwear retailer on the planet, these are some of our favorites:

A Final Thought

As a presumably aspiring well-dressed man, it behooves 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.