How to Wear Chukka Boots | 8 Styles For Every Guy

Chukka boots are strange beasts. With their unstructured toes, low-cut uppers, and thin soles, at first glance they are more like a high-top sneaker than a burly boot. Many brands describe them as half boot, half shoe. And to many customers, that makes them the ultimate piece of footwear.

When it comes to styling chukkas, the model has become popular enough that the market has both classy and casual variants, though the general consensus is they top out in smart casual environments, not being nearly dressy enough for formal wear.

To help you wear chukkas, we’re going to look at their benefits, history, popular ways to style them, and lastly, a few of the best chukkas.

clarks desert boots casual
via @okalaninui on Instagram in his Clarks Desert Boots 

How to Wear Chukka Boots: Overview

  • Suede is the most versatile
  • Stick to lighter suedes for casual wear, glossy leathers for more formal wear
  • Avoid wearing with a full suit and tie

The short uppers, unstructured toe box, and crepe sole make chukkas a great casual boot.

For rocking a casual look, you can team suede chukka boots up with a t-shirt and slim black jeans, for example. If it’s chilly, layer up with a bomber jacket or Harrington.

When smart casual outfits are the order of the day, you may wish to pick a smooth, slightly shiny leather like Thursday’s Scout in Brown with some chinos.

Not every pair of chukka boots is suitable for business casual outfits or business casual occasions. For these circumstances, you are better off opting for black chukka boots or darker suedes.

And chukkas don’t really work for a formal occasion that requires a jacket and tie. For that you’ll want a dress boot, but in a pinch, you could pull off a glossy black leather Chukka like Thursday Boot Company or Carmina.

[Related: The 10 Best Dress Boots]

clarks desert boot upstate fashion
via @upstateguystyle on Instagram

Benefits of Chukka Boots

How many other types of clothing or footwear allow for so many outfit ideas? Very few, when you take the time to think about it.

They’re Inexpensive Boots

Chukkas are often unstructured and shorter than other boots, plus bootmakers use fewer materials to make them, lowering the price. When comparing a brand’s chukkas to their 6-inch boots and Chelseas, you’ll always find the chukkas to be cheaper.

They are often the least expensive boots you can buy, and you can pick up a pair of Clarks for under $100 on sale — that’s pretty inexpensive for a boot.

They’re Versatile Boots

When deciding how to wear chukka boots, you can be fairly sure that whatever you wear will get it right. Ultimately, a pair of chukka boots gives you timeless style no matter what you wear, including:

  • dress pants
  • black jeans
  • casual wear
  • a button-down shirt
  • a dress shirt
  • a sport coat
  • Cashmere sweater or cuffed jeans

Just remember that if you’re going casual, stick to lighter colored suedes to keep things informal. 

[Related: 5 Ways to Style Red Wing Boots]

 

Chukka Boots: Background

  • First seen in World War 2
  • Based on boots worn for playing polo

Chukka boots, often called desert boots when they’re suede with crepe soles, can trace their heritage back to the British Army’s North African campaign of World War II. During the Western Desert Campaign, desert boots worn by the “Desert Rats” earned a reputation for being comfortable and durable.

But the desert boot did not emerge out of thin air. It was very much based on polo boots, the stylish footwear favored by aristocratic horse riders while riding their polo ponies.

Whether you want to know about leather chukkas, brown chukka boots, suede chukka boots, desert boots, or if you should opt for a crepe rubber sole or leather sole, our guide will ensure you find the style that works for your tastes.

[Check out: The 10 Best Desert Boots You can Buy]

Jadd Desert Boots
Image Source Jadd Shoes

Chukka Boots vs Desert Boots: Aren’t They the Same?

  • Desert boots are chukkas made with suede uppers and crepe rubber soles

Yes and no. Let’s take a look at the differences.

What you can say definitively is that desert boots are a form of chukka boot. Generally, the desert boot is lighter in color, made of suede, and comes with a crepe sole.

Some chukka boots can be made with thick, full grain leather and even cordovan, and can be made with more high end soles like Dainite or leather.

When you wear chukka boots, particularly suede chukka boots, they’re often mistaken for desert boots and vice versa. The terms are now used so interchangeably as to be practically indistinguishable for the average guy.

In short: not all chukka boots are desert boots, but every desert boot is a chukka.

[See my review of the Clarks Desert Boot]

Clarks desert boot featured real
The Clarks Desert boot

Tips on How to Wear Chukka Boots

As mentioned earlier, chukkas are primarily a casual boot, but that doesn’t mean there’s only one way to style them. Nor does it mean you can’t look classy and casual at the same time.

Casual Occasions

Chukka boots are great for pulling off a casual look when you don’t wish to wear taller, more structured boots.

They’re perfect for pairing with jeans and an untucked button-down shirt under a jean jacket. 

We’re going to start by looking at very casual outfits and move to dressier options that work well with chukkas.

[Related: Chukka vs Chelsea Boot]

Thursday Scout Chukka and jeans
Image Source: @thursdayboots

The Rebel: with a suede or leather jacket and jeans

This roguish look incorporates a leather jacket, well-worn jeans, and a dark shirt.

Ideally, you’ll match the leather of the chukkas to the jacket: brown suede with brown suede or black leather with black leather.

The undershirt and jeans should contrast with the jacket and chukkas. If you have darker leather, go for lighter jeans and t-shirt. (We’ll allow a black shirt with a black jacket, but make sure the jeans aren’t black too.) 

Accessorise with a watch and sunglasses. Necklace is optional.

clarks chukkas textured sweater
Image: @clarksshoes Instagram

The Nautical Look: with a textured sweater

Combining chukka boots with a chunky sweater is something of a no-brainer. Maybe a thick sweater makes you think more of thick boots, but you’ll find the combination works well and adds nice pop to your outfit that’s just a sweater and chinos. It’s an easy win, especially if you trick out the look with accessories like a classic wristwatch, a simple bracelet, or vintage-looking shades.

With their informal look and the texture they add, suede chukka boots great with this fit. Team up with a pair of corduroy trousers for more texture. 

Clarks Chukks and Streetwear
Image Credit: @clarksshoes Instagram

The Street Look: with a pullover  and hooded jacket with dark jeans

No one will bat an eyelid if you turn up wearing dark suede boots tag-teamed with a hooded sweatshirt and dark trousers. The trick, again, is to pick a desert boot style: suede and a white crepe sole to keep things informal, but consider a black, grey, or green colored boot to make things a little less vintage and more streetwear-friendly.

This dress-down-but-stylish look can easily see you a night out at the pub for watching a soccer game in the rain.

Smart Casual

Almost any chukka boot and material color can be pulled off when you need to go smart casual. So long as you keep a good balance between every piece, you will avoid fashion faux pas.

If you prefer suede for chukka boots, go for a casual brown leather. A napped shoe will look better with pants and shirts for more conservative or preppy affairs, and brown suede is a staple of the smart casual realm when paired with khakis or white chinos. But you can fall back a little with a hunter’s jacket and a worn leather strap on your wristwatch.

[Learn more: How to Pick the Best Leather for Your Watch Strap]

Harrington Jacket and Chukkas
Image Credit: @james_bond_style_ Instagram

The Mod Look: with a Harrington jacket

A staple of mod culture is combing a pair of chukkas with a Harrington Jacket.

Avoid black chukka boots paired with brown and vice versa. Chukka boots in earthy shades and tawny colors are a safe bet and work well with almost everything you may have in your wardrobe.

Popularized by Elvis Presley and James Dean, the casual Harrington jacket is the slightly less edgy version of a jean jacket. It works perfectly with a pair of suede Chukka boots.

[Related: Why the Harrington Jacket Works On Anyone]

Chukkas Ivy Look
Image Credit: @clarksshoes Instagram

The Ivy Look: monochromatic with a plaid jacket statement piece

This combination will be a definite showstopper in the fall. It exudes am autumn palette and an outdoor vibe with the merest of Ivy League undertones.

The key here is your choice of color: go for warm, earthy hues that reflect nature in your clothing, then pair it up with dark and brooding leather chukka that complements the Americana and seasonal aesthetic.

Also vital to the look is your choice of plaid coat. Select something that looks well structured and thought-out. It is the pivot upon which every other piece in your ensemble hangs. If you’re willing to spend serious money on the highest quality tailor-made coats, check out (or just find some inspiration from) Articles of Style

Chukkas linen suit
Image Credit: @clarksshoes Instagram

The Refined Casual Look: with a linen suit

Perfect for a slightly dressier summer look the linen-suit-and-chukka combo is a classic, somewhat dressed-up outfit.

Linen brings texture and class that pairs well with a light suede Chukka and textured polo shirt.

This style should be very monochrome, and texture does the heavy lifting. The uneven appearance of the linen, the nappy suede, and a lighter-colored rib t-shirt or button down avoid the unpleasant matchy-matchy look you would get with other single-color outfits. 

[Related: The Best Lightweight, Short-Sleeve Shirts for Summer]

Business Casual

When you need to get down to business, stick with chukka boots made with smooth leathers. Pointed-toe boots or sleek toe boxes are more appropriate for business, if you can find a dressier model like Carmina or Crockett & Jones.

Leather soles are the wisest option, but this is very much down to personal preference. Still, select something with a flat profile like leather, Dainite or Ridgeway, or cork — no luggy Commando soles, please. 

Dress appropriately for the prevailing dress code of your workplace and clients. You neither wish to be over or under-dressed.

[Related: The 8 Boot Soles You Should Know About]

Carmina Bootmaker Chukkas, business casual
Image Credit: @carminashoemaker Instagram

Classic Office Attire: with a white button-down shirt, dark trousers

The modern office look takes different classic business pieces and reinvents them for a contemporary context. This, then, makes leather chukka boots a perfect accompaniment.

A striped button-down shirt evokes ’80s Wall Street and should be paired with a preppy style tie. However, it can come across as slightly dated, and from an image perspective, carries significant baggage.

For a more updated look, a modern-fit black jacket and a contrasting gray pants duo will give you more youthful optics in the style of Thom Browne.

business casual desert boots
via @sartorialchap on Instagram

Classic Business Casual: Dark Shirt or Jacket & Khakis

This look is focuses on your accessories and hints that you are off to do something interesting at the close of business. Go for a regular fit, dark-colored shirt and contrasting light pants for warmer months.

Wearing a breezier Friday business look is a deliberate understatement that frees up space to experiment with accessorizing. For this, think cool shades, an elegant briefcase, and the obligatory chukka boots.

Clarks Desert boot shorts

When You Shouldn’t be Wearing Chukka Boots

Nowadays, chukka boots are permissible for most occasions, albeit dependent on their styling and color. There are two clear no-goes for wearing chukkas.

  1. This should be obvious: don’t wear chukkas when going to the gym.
  2. Don’t show up at a formal event wearing your comfy chukkas.

Chukkas may be acceptable with a linen suit, but generally speaking, chukkas are just too casual to wear with a suit. There’s wiggle room if you’re not wearing a tie, but only if it’s not a black suit.

It’s possible to match these with summer shorts instead. But conversely, shorts look goofy with black full grain leather boots. If you’re wearing them with shorts, do suede chukkas — just know that about half of all “fashion guys” can’t be convinced that any boot can be worn with shorts.

Should You Wear Chukkas to Work?

In business settings, what’s your company’s dress code, who are the clients, and where do you plan to meet them. If the code is anywhere between casual and full suit, you can make chukkas work with the advice we gave in this article. But they aren’t ideal if you need to wear a jacket and tie.  

How to Wear Chukka Boots: 3 Great Ideas for Jeans

Pairing up chukka boots and jeans is the most obvious combination because of the combo’s versatility. They are effectively a tent pole on which to throw your canvas of shirts and exterior layers.

Feel free to supersize with a roomy scooped neck top and well-tailored jeans, then anchor the entire outfit with a trendy pair of chukka boots.

Navy Jonh Lofgren Desert Boot and Jeans
Image Credit: @johnlofgrenbootmaker Instagram

Raw Denim

You can easily compliment any jean with almost any chukka boot style, with the possible exception of baggy, torn jeans. But if the ensemble looks balanced, you are unlikely to hear from the fashion police.

For instance, you can pop on your desert boots with a pair of raw selvedge denim jeans, a blazer, and quality button-down, and you will look the part.

Broadly speaking, the greater the formality, the darker the jeans should be.

High end Japan-based bootmaker John Lofgren makes lovely Desert Boots in a variety of cool leathers at around the $500 mark.

[Shop the luxury John Lofgren Desert Boot in 4 colors here!]

Clarks desert boot featured

Casual Denim

Simply adding an extra layer to your casual outfit can lift an otherwise straightforward ensemble, and a few simple moves can make all the difference. Tuck in your shirt to reveal your chukka color-coordinated belt and leather watch strap, for example.

Stick to a theme and limit shade variation for a more minimalist and clean aesthetic that appears as effortless as it is casual.

All-Denim Outfits

How do you get away with the double-denim look without resembling a cowboy?

Try different colored denim, a streamlined wristwatch, and ice-cool chukkas.

Loose, lived-in suede boots finish off this western look without going too cowboy, and be sure to wear well-fitting jeans to bring a modern, urban twist to your outfit.

[Related: In Defense of the Canadian Tuxedo]

clarks desert boot style
via @menswearupdate on Instagram

Dapper Denim

The sum of the dapper jeans look is more than its individual parts. This is why the look is so timeless.

The dapper look hinges on perfectly fitting blue jeans that are neither too baggy nor too tight, both too juvenile for the look you’re trying to pull off. A pale pocket square adds to the retro-chic you are going for.

A pair of business-like chukkas with subtle pebbling will set everything else off without being too polished. All of the pieces you put together shouldn’t be too fancy. You are going for a well-thought-through if understated, a combination that gels.

Chukka Boot Types and Our Top Selections

Great for formal occasions and more hard-wearing than suede, smooth leather chukkas can be equally at home in business casual settings as your daily footwear. Eventually, top-quality leather chukkas settle into a distinctive, rugged patina and will last for years. Darker, polished boots will look more sophisticated. 

Leather or crepe sole?

In formal settings, the default is leather soles. You can get away with Dainite or nitrile cork if you want some more grip while maintaining the all important flat profile.

That’s just if dressiness is a concern, though. Crepe soles are on-trend for smart casual or dress-down Fridays if it has a distinguishable heel. Crepe is among the softest soles and extremely comfortable. Just know that it’s also one of the least durable, and thinner ones don’t perform great in wet weather. 

thursday scout boot
Image Source: Thursday Boot Company

Best Value Chukka: Thursday Boot Scout

Thursday makes an astonishing twelve versions of their Scout boot. You can get them in WeatherProof suede and their Rugged & Resistant leather. The Rugged & Resistant leathers come in a flat and hardy wedge sole, while most of the rest have studded rubber soles.

Suede chukkas are more casual than conventional leather counterparts, but the texture of suede adds a lovely variation that elevates any outfit.

Suede is also ideal for the spring and summer months, as the softer look and texture look great in light or muted colors. If you’re in very hot weather though, you may not love Thursday’s leather leather lining and might want to opt for a Clarks chukka — but Thursday’s leather lining is very soft on the feet and adds body to the boot. 

thursday scout boot gray suede

As with smooth leather boots, suede chukkas should have distinct heels for formal occasions rather than crepe or rubber soles. Thursday offers both.

This company definitely offers the best value in the game, offering resoleable construction and leather lining, two features that you won’t find on Clarks, for just $149.

[Shop Thursday Boot Company’s Scout Here]

As the suede variants are made from Thursday’s suede protector WeatherSafe material, these chukkas have been waterproofed and treated with a water-resistant solution for superior wet-weather performance.  

Thursday Boots focus on sustainability and fair labor. All their cowhide comes from top-tier American cattle, and the company exclusively works with tanneries that are highly regarded by trade body, Leather Working Group, for their safe chemical management and environmental practices.

Most Comfortable Chukka Boots: Clarks Bushacre 2

Without a doubt, Clarks’ Desert Boots are the iconic chukka. For its Bushacre 2, the renowned footwear company reinvents the chukka boot in gorgeously rich leather.

Excellent quality

Thanks to their rubber outsoles, the Bushacre is significantly tougher than the crepe soles of old. But the uppers are famously supple and thin enough to limit any tough break in. Thanks to liberal waxing, they’re also reasonably water-resistant.

If you’re hunting out an inexpensive pair of leather chukkas that last longer than their original Desert Boot, you won’t go wrong with Clarks’ Bushacre 2 range.

[Love these shoes? Grab the cheapest pair here!]

From Desert Sands to Your Shoe Tree

The desert boot is the most versatile of footwear. They look fantastic with a pair of dark jeans and t-shirt and with chinos and a blazer. (And they are even better when you accessorize or add an extra layer.)

And today, chukka boots are not limited to polo players and World War soldiers.

Now that you’ve got learned everything you need to know, go out and grab yourself a pair of what will soon be the most versatile shoes in your wardrobe.

FAQs

Is it okay to wear chukkas and dress pants?

Yes, dress pants with dark leather chukkas will not cause a stir in the office, though it's best to avoid chukkas at formal (think suit-and-tie) occasions.

Are chukka boots suitable for summer?

Suede chukkas in tan, buff and light gray are great style decisions for warmer summer weather. Go for unlined suede for the thinnest, most breathable upper material.

Which socks are best to go with chukkas?

For a more traditional appearance, choose cotton or thin woolen socks that coordinate with your pants. To cut a dash, opt for bold, bright colors or patterned socks that coordinate or complement your outfit when you wear leather chukka boots. When worn more casually, some guys like to wear no-show socks — just remember the boot's collar might chafe a bit.

What's a suede eraser?

Most chukka style suede boots can get stained. An eraser is a block used for stain removal. It's similar to a pencil eraser, but not identical.

Where does the name chukka boots come from?

Chukka boots are a salute to the horse riding jodhpur boots used by polo players. The term chukka is a time interval of play during a polo game.

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Karl Wasson

Karl is an IT product manager living in South East Asia who gets a kick out of durability and dependability. He believes form and function are not mutually exclusive. When he's not working, he's searching for the best bespoke menswear in South East Asia and beyond.

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