How to Wear Chukka Boots: 8 Ways

The chukka boot is a staple for any man’s wardrobe. Stylish and versatile, the chukka boot isn’t just reserved for one type of wear. Whether you’re looking for a way to polish up a casual outfit or an alternative to wingtips for wedding season, you’ll want to be sure you’ve got a pair on standby in your closet. 

What are chukka boots exactly? These classic boots often have suede or leather material, are ankle-height, and feature rubber or leather soles with 2-3 open-faced eyelets. Because of the different material options, these boots can offer a variety of casual wear, smart, and business looks.

Find out our favorite ways on how to style chukka boots throughout the seasons below.

#1 Desert Boots with Fitted Jeans and Flannel

Ranging from a light suede to the darkest of leathers, chukka boots pair well with the autumn weather—and so do their casual cousin, the desert boot. 

Desert boots and chukka boots are easy to mix up. To put it simply, all desert boots are chukka boots, but not all chukkas are desert boots. Desert boots offer a more laid back vibe and often feature rubber soles and sandy leather uppers. 

With that said, you won’t find an easier masculine look than a nice pair of fitted jeans and a mackinaw flannel jacket. Or, if you’re not a fan of flannel jackets, you can opt for a linen button-down with earthy colors instead. Pair this with some sandy or light brown desert boots and you’ve got a well-polished but casual look for just about any weekend plan.

#2 Semi-Formal Matching Shirt and Boots

If you’re looking for a fall look that leans more into the realm of sophistication, you’ll want a dark leather chukka boot for a semi-formal alternative. Investing in the right pair of chukka boots is all about knowing what style to wear and when.

To feature the autumn colors in your wardrobe, pair maroon leather chukka boots with a two-piece tweed suit and a maroon shawl-collar sweater. If you decide to dress it down, match a merlot-buttoned shirt with burgundy leather boots.

When selecting chukkas for fall it's also important to understand the versatility of the boot to be sure you’re wearing them the right way. Here are a few factors worth noting as you’re selecting your outfit:

  • The shade of boot – Typically, you’ll want to reserve the lighter suede chukkas for the more casual summer and spring-colored outfits. In the fall and winter months, however, your dark leather chukka boots will match more cozy attire.
  • The material – Leather chukkas are more durable than suede and have a tendency to show less age, making them suitable for either work or leisure. Men’s waterproof boots like the suede chukka boots, on the other hand, are a slightly less rigid option and come in a number of other shades like greys, blues, and greens.
  • The occasion – For more formal occasions, stick to dark leather chukka boots for a dress shoe substitute. Meanwhile, light leather and suede chukkas offer a more casual look in any season. Another component to consider is the sole, with thicker soles tending to be more casual and thinner soles more formal.

#3 Paired With Dress Pants and a Sweater

In the winter months, your darker chukka boots can pair with just about any outfit. If you live in an area with snowfall, you might want to consider sticking to leather chukkas for durability and warmth whenever you’re out and about.

Wanting to dress up, but still be comfortable for the holiday dinner? You can pair dark grey wool dress pants or trousers with some dark brown or maroon leather chukka boots for a smart casual look. Add a bit of vibrancy with some patterned cotton socks—or a pair of rustic wool socks for warmth.

For shirts, we recommend monochromatic sweaters. Try a winter white or cream-colored waffle-knit sweater, for example. You can also add some texture with an Irish Aran sweater—the fisherman sweater—for a popular revival.

And once the dinner is over, you’ll want to make sure your outfit is complete with a well-coordinated jacket. We recommend a long pea coat to stay slightly more formal, or a hooded parka for a more casual vibe. 

Pro tip: Check out our latest blog on How to Tie Boots in 4 Ways if you’re looking for ways to spice up ways to tie your chukkas.

#4 Paired With Dark Jeans and a Utility Jacket

The next outfit is a perfect companion for the balmy winter days. Dark leather chukkas can work well with rolled or cuffed dark navy jeans. To best utilize this pairing we recommend an outfit like this:

  • Dark brown leather chukka boots
  • An insulated utility jacket—either grey-green or brown
  • Fitted and flexible dark wash jeans
  • A simple cotton henley or long-sleeve tee

For even more options, this outfit can work by switching up the colors of the utility jacket or underlayer, allowing you to mix and match for more results.

#5 Go All Denim

With springtime flowers come new ways to wear your chukka boots. And with the spring colors, you’ll be able to wear suede chukkas to round out many of your outfits. 

Although, as you know, the weather is rarely a smooth transition from winter to spring. That’s why we’ve got you covered with this look:

  • Sandy suede chukka boots 
  • A light denim shearling jacket
  • Dark or light jeans 

This combo is our bold, urban choice for chilly spring days. And if you’re looking for some extra warmth—or want to evoke more of a streetwear aesthetic—you can add a grey or graphic hoodie underneath the denim shearling jacket. 

Take a different approach and match your light to darker brown suede chukka boots with a denim button-down and deep blue denim jeans for a modern ensemble. We like this look best with some rolled-up sleeves and a minimalist watch. 

#6 Take It Smart Casual With Chinos

By mixing casual and formal, these spring outfits are ideal for a Friday at the office. Especially in the warmer months, you can mix and match your favorite pair of suede chukka boots (we recommend greys or navy blues) with a pair of fitted chino pants, and an Oxford button-down to complete the look.

If you like the country-club style, consider pairing some lighter chinos and brown suede chukka boots with a seersucker blazer over a button-down. And if you need to get more formal for a Sunday brunch, try a khaki blazer with the suede.

#7 Keep It Simple With Utility Pants and Desert Boots

Despite what you may think, you won’t have to leave your boots in the closet when the summer comes. On those summer days when the air is a bit cooler, you can try combining a pair of fitted utility pants with some beeswax desert boots. For some nice color combinations with the brown beeswax leather boot, try a mid-range cargo brown or even an olive green shade.

For shirts with this look, we like a lighter short-sleeved henley shirt—with blues and creams for brown pants, and greys and whites for olive pants. Or if you’re in search of a more dramatic look, you can swap out the henley for a scoop neck t-shirt.

Wanting to mix up your wardrobe with some other options for the summertime? Try out a few of these combinations we’ve put together:

  • Chinos and beige boots – Like our springtime look, white chinos and beige boots can offer a breezy, laid-back beach vibe for any outfit. Style this with a patterned or simple-color tropical shirt and you’ve got a winning look for a weekend on the coast.
  • Pearl grey pants and tan leather – For business professionals, pairing tan leather chukka boots and slim-fitted grey pants can be a trendy option for the sunny summer days. Try this look with a structured oxford and club tie to complete this sharp setup.
  • Jeans and black leather chukkas – We like to call this look Hollywood casual. Try on any pair of slim-fitted jeans and pair them with black leather chukka boots. Finish the look with a simple crew-neck white t-shirt and aviators for a simple, but slick taste.

#8 Be Bold With Shorts and Suede

Flattering with the right boot choice and style, suede chukka boots and shorts can be a bold choice to cool off when the weather is especially hot. You’ll want the right fitted shorts—falling just above the knee—and your favorite pair of tan suede boots to elevate the overall look. 

Try a simple short or long sleeve cotton shirt with a leather watch as an outfit for walking around town. Headed for a more hipster style? We like a bold orange or mustard beanie with a green button-down shirt, shorts, and sandy suede chukkas.

As summer descends into the music festival circuit, you can go boho with a faded denim jacket, striped shirt, and khaki shorts. Light suede desert boots are the perfect pairing for this contemporary look. Finish it off with a brown panama or wide-brimmed hat, a desert-patterned leather bracelet, some aviators, and you’ve got a winning outfit worth celebrating.

Stylish Chukka Boots from TOMS

Feeling inspired? TOMS has a diverse selection of chukka boots and more to choose from. You can round out your wardrobe and test out some of these looks by shopping our men’s boots collection today.


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Reviewed By Dan Caves

Dan Caves is the Senior Manager of Digital Marketing at TOMS and has been operating in the digital space for 6 years, writing about the latest trends or styles and helping brands make bold statements with innovative tactics and creative concepts. He's determined to go all the places, see all the things, and pet all the dogs.