How To Wear Chukka Boots (2021 Men’s Style Guide)

As a must-have casual boot for men, chukkas boots have become a wardrobe staple that will elevate any ensemble. Chukka boots are a classic style of footwear that look stylish, feel comfortable, and work well with all types of outfits. These boots can be made from suede or leather, and guys can choose from a range of colors, with black and brown being the most popular options.

Whether you’re going out for date night or want a smart casual look for the office, chukkas offer versatile and fashionable shoes you can wear with everything in your wardrobe. Some men will style chukka boots with jeans and a t-shirt for a casual look, while others may prefer to dress up these boots with chino pants, a button-down shirt and blazer for a business casual outfit that will impress.

With so many styles and trends, it can be a challenge figuring out what to wear with your chukkas. To inspire you with outfit ideas, we’ve compiled a guide on how to wear chukka boots. From black to brown and suede to leather, explore the best Chukka boots outfits to find trendy styles you’ll love!

Chukka Boots Outfits

What Are Chukka Boots?

Chukka boots are a classic men’s boot style featuring suede or leather ankle-high uppers, rubber or leather soles, and two to three open-laced eyelets. Chukkas are often made with leather or suede, and most commonly come in brown or black. As the most popular style, suede chukka boots are cool and textured, offering a balance between rugged and elegant styling. Most guys wear brown chukka boots with casual outfits and black leather boots with professional or semi-formal clothes. Light colors are often associated with more relaxed styles, while darker shades are sleek and classy.

What Are Chukka Boots

When thinking about these boots, there are many different types of chukka boots to choose from. Guys can choose from casual rubber soles or smart leather soles, a pointy toe for a more formal design or a rounded toe for a simple look, and thick laces for a work boot aesthetic or thin lacing like dress shoes. When dressing up chukkas, you’ll want to pair dark cuffed jeans or dress pants with a button-down shirt and jacket.

Chukka Boots vs Desert Boots

Desert boots are a type of chukka boot featuring textured crepe rubber soles and lighter color leather. The difference between chukka boots and desert boots is that desert footwear is made with a soft, thick rubber sole and generally comes in a light brown or sand color. The classic and more formal dark chukka boot is commonly designed with hard, thin leather soles. While some brands use the terms interchangeably, not all chukka boots are desert boots but all desert boots are chukkas.

Desert boots are comfortable and casual, and look good with utility shirts, work pants, and aviator jackets. For an easy and masculine outfit, combine suede desert boots with fitted jeans, a linen button-down, and a Mackinaw flannel jacket.

Still respected and worn by stylish gentlemen, Clarks created the original desert boots. Trendy guys can experiment with popular brands like Oliver Cabell, Tod’s, Barbour, and Lemaire.

Desert Boots

Chukka Boots Styles

Leather Chukka Boots

Leather chukka boots are more formal and durable than their suede counterparts, and will look great with many different outfits. An excellent investment, quality leather boots will last for years and many develop a dignified patina over time. While black leather chukka boots are the most common design, brown leather chukkas offer an elegant and versatile option. You’ll often see men sport a dark pair of well-polished, thin-laced chukkas at the office or with cocktail attire.

Leather soles are the best choice in professional settings, but crepe soles are perfectly acceptable for business casual outfits as long as your footwear features an observable heel. To find classy leather chukkas, a dapper gentleman will seek out high-end brands like Magnanni and Becket Simonon.

For a comfortable and fashionable approach, leather chukka boots style well with simple denim jeans and a t-shirt. Light brown leather is ideal for casual looks with blue jeans and a top, while dark brown or black chukkas are preferred for smart casual and business styles that pair dark jeans or dressy chino pants with a button-down shirt and jacket.

If you want to casually wear a layered outfit, you can add an open military shirt, flannel or hoodie. In the fall and winter, guys may want to wear a bomber jacket or heavy coat. When styling leather chukkas to create a casual look, you can choose rubber or crepe soles without a heel.

Leather Chukka Boots

Suede Chukka Boots

With their distinguished napped aesthetic, suede chukka boots are must-have footwear for elevated casual outfits. Suede chukkas are stylish, easy to wear, and provide a rugged manly aesthetic. The leather construction is lush, but the texture and simple lines are effortlessly chic. With so many shades, guys can choose from black, brown, sand, tan, navy, dark olive and ash as well as a range of other colors. These shoes can be dressed up or down depending on the occasion and your style.

You’ll generally find well-dressed guys pairing suede chukka boots with jeans for an everyday casual look. For a fall brunch outfit, combine suede chukkas with dark cuffed jeans, a henley shirt or sweater, and a denim or bomber jacket. On colder days, add a fitted leather biker jacket for a cool and rebellious vibe, or a pea coat for something more classic.

Use suede chukkas to round out smart casual outfits during warmer months. In summer and spring, style light grey suede footwear with chino pants and your favorite color Oxford button-down. If you like a country-club aesthetic, add a seersucker blazer for a classy touch. For an understated yet posh outfit, a khaki-colored blazer will complement your suede boots and dressy trousers. When shopping for your first pair of chukkas, we highly-recommend getting suede boots for maximum style and flexibility.

Suede Chukka Boots

Brown Chukka Boots

Brown chukka boots are effortlessly cool and casual shoes, and guys can wear these boots with anything in their closet to create the perfect outfit. Dark brown chukka boots are excellent for smart and business casual styles when you want to dress up your look. Light brown chukkas style nicely with simple and timeless combinations like jeans and a t-shirt or chinos and a loose button-down.

With brown footwear, you can’t go wrong with suede or leather, although brown suede chukkas are universally-flattering and leather is typically associated with more elegant fashion. This trend can change when the shoe color is paired with rubber, crepe or leather soles. You’ll also want to note that lighter shades complement bright summer wardrobes while darker brown boots are better-suited for fall and winter.

With its distinct textured hue, beeswax brown looks stylish with crepe soles. If you’re going for a military-inspired casual look, you can’t go wrong with beeswax leather chukkas. If you want to go for a lighter shade, a heavily napped taupe-colored suede is another perfect partner for a masculine, utilitarian-chic outfit. Great for summer and spring, tan and beige boots have a laid-back sophistication that dresses well with chinos and preppy-style tops. By color-matching your beige boots to your pants, you have room to experiment with your shirt.

Rustic and stately, dark brown chukkas can be paired with relaxed and semi-formal clothing. You’ll want to experiment by combining a deep mahogany round-toe chukka boot with regular-fit jeans and a flannel. Take your appearance to the next level by partnering pointed-toe dark walnut boots with olive trousers, a crisp button-down top, and a stainless steel sports watch.

Brown Chukka Boots

Black Chukka Boots

Black chukka boots always look good for a sleek and classy style you can wear with casual, business professional and formal outfits. Timeless and fashionable, black boots are popular footwear for men who want versatile shoes that will pair nicely with everything in their wardrobe.

For an urban-chic look, wear black boots with an all-black outfit consisting of slim-fit jeans and a fitted crew neck shirt. You can feature a bright-colored oversized puffer jacket and a beanie for a cool street-inspired outfit. For a modern trendy style, consider a tan suede or thick sherpa-lined denim jacket and accessorize with some aviator sunglasses.

For a business professional or formal look, you’ll need to combine pointed-toe boots with a tailored gray suit. While this may seem like a clash of styles, chukka boots with a suit have become a fashion trend worth considering. Guys can take this outfit up a notch by color-matching a well-structured trench coat to their boots. This will round out the whole look and add a chic edge to a classic look. Since black is the most versatile color, you’ll want to experiment with different soles, lace styles, and heel heights to find the combination you’ll use the most.

Black Chukka Boots

Chukka Boots Outfits

Casual Chukka Boots Outfits

Chukka boots are an excellent way to level up everyday casual outfits for an easy and stylish look. These naturally casual men’s boots are popular with jeans and a t-shirt or chino pants and a button-down with a cool jacket. When styling casual outfits with chukka boots, you’ll want to pick a suede style in a brown color to get the right aesthetic.

For a simple and flattering summer style, you can try pairing a short-sleeved henley shirt with fitted utility pants and beeswax desert boots. To take your chukkas to the next level for a polished finish, you can wear dark blue denim jeans and a white button-down shirt with a fitted denim jacket. For a more youthful approach, trade the button-down for a scoop neck t-shirt for a more relaxed yet edgy vibe.

Casual Chukka Boots Outfits

During the fall and winter, put on a long-sleeved shirt and thick outerwear for a thicker, masculine silhouette. Some trendy guys may choose a deconstructed pea coat or melton jacket to match the simplicity of the chukkas. For a modern take on outdoor-casual, style dark brown leather chukka boots with light blue jeans, a linen-button down, and an oversized sheepskin coat.

Casual Outfits with Chukka Boots

Smart Casual Chukka Boots Outfits

You can dress up chukka boots and create cool smart casual outfits for a modern and fresh style. For an elegant and stylish look, start by wearing beige suede boots with warm-toned twill pants, a band-collared button-down shirt, and a fitted shawl sweater. Practical and versatile, you can also pair dark brown leather chukkas with cuffed jeans, a fitted crew neck t-shirt, and a trendy jacket.

Smart Casual Chukka Boots Outfits

When styling a smart outfit you can wear on dates or to bars after work, combine black leather chukkas with dressy pants, a dress shirt, and a tailored blazer to achieve a sharp modern look. Designer sunglasses and leather-strapped watches will complement your style, and you can match colors on different pieces to bring the ensemble together for a classy finish.

Smart Casual Chukka Boots

Business Casual Chukka Boots Outfits

Chukka boots can add a modern and dashing touch to business casual outfits as long as you keep your footwear polished and professional. Black leather chukkas go perfectly with dark trousers, a crisp white button-down shirt and blazer. You can finish this look off with a luxury sport watch and a full-grain leather belt. For a more casual look on Friday, you can neatly fold your sleeves up for a style that’s sexy but still professional. Young gentleman can also pull off dark pants, a button-down top and sweater over with dark brown leather boots for a sharp and sleek ensemble.

Business Casual Outfits with Chukka Boots

A professional business look during the hot summer months calls for tan leather boots with pearl gray slim-fit dress pants and a well-structured Oxford shirt. Add a classic club tie and a tan near-sheer pull-over to complete the clean-cut aesthetic. If you need a timeless business casual style in the fall or winter, you can’t go wrong with dark brown suede chukkas with dressy chino pants, a button-down shirt under a sweater, and a complementary blazer.

Business Casual Chukka Boots Outfits

Semi-Formal Chukka Boots Outfits

Fashionable men can use chukka boots as a modern alternative to traditional dress shoes for the perfect semi-formal look. Whether you prefer dark brown suede or black leather chukkas will determine how you wear your boots to create the right outfit. For classy upscale styles, combine black full-grain leather boots with a well-tailored two-piece suit, a white shirt, and no tie.

Chukkas and Suit

You can also add a sophisticated and chic pop of color by subtly matching your shirt with your boots. To accomplish this, you might pair a beige or champagne shirt with dark honey brown chukkas or a merlot shirt with dark burgundy boots. For a semi-formal style in the fall, combine maroon leather boots with a two-piece tweed suit over a maroon shawl sweater.

Semi-Formal Chukka Boots Outfits

Chukka Boots with Jeans

Chukka boots always look great with jeans, giving guys the ability to style casual and smart casual outfits for a universally-flattering look. The most popular way to wear chukkas is with jeans and a t-shirt, but this ensemble can be styled to fit your desired aesthetic. For a strong and confident look, style brown suede boots with classic regular fit blue jeans and a shirt or flannel for a masculine relaxed vibe. When dressing down, you’ll want light colored desert boots for the right texture and manly finish.

Chukka Boots with Jeans

To dress up your chukkas, combine your dark leather boots with fitted jeans, a nice sweater, and a bomber jacket. You can also pair black chukka boots with skinny dark or black jeans, a black or blue shirt, and a leather jacket. To create a fashionable outfit suitable for date night, sport polished leather boots with dark fitted and cuffed jeans and a gray tailored blazer.

Chukka Boots with Jeans Outfits

As far as your top, a classic button-down shirt is an elegant and tasteful approach, while a slim-fit henley is sexy and flattering for most body types. Chukkas with jeans offer the perfect canvas for men who want to experiment with layers and outwear such as sweaters, jackets, and scarves.

Chukka Boots with Black Jeans

Chukka Boots with Chinos

Chukka boots and chinos are a natural fit when styling casual and smart casual looks. Brown suede chukkas with khaki chino pants work well with less formal outfits, while dark leather boots are ideal with dark-colored pants for more upscale events. Get a clean cut look by pairing dark brown leather chukkas with classic-fit brown chinos, a lightweight check shirt, and a high-collared leather jacket. For an understated version of this style, swap out the leather jacket for a canvas one. You can accessorize the ensemble with with your favorite sunglasses.

Chukka Boots with Chinos

For a cool and refined vibe, khaki pants and a half-tucked chambray shirt partner excellently with brown desert boots. For a preppy and classy take on this outfit, you’ll want to go for a bright plaid shirt, a full tuck, and a sport watch with a white dial. Fashion-forward men can combine light gray suede boots with white chinos for a modern take on winter white. To keep warm in the winter months, put on a heavily-layered top consisting of an Aran sweater, a textured sport coat, and a wool melton coat for a dynamic and trendy silhouette.

Chukka Boots with Pants

Chukka Boots with Dress Pants

A perfectly sophisticated combination, chukka boots with dress pants is an effective visual balance of masculine and delicate aesthetics. For a sleek and unique party look, guys can pair beige suede chukkas with slim gray houndstooth dress pants and an open fitted henley shirt. Fashion a cool street style by partnering pointed-toe leather boots with European-cut dress pants and a fully tucked-in white button-down shirt. You’ll need to choose a luxury watch with a unique ostrich or snake leather strap to complement this super sexy aesthetic.

Chukka Boots and Dress Pants

Simple and effective, leather chukka boots are perfect to wear with classic dress pants and tailored button-down shirts. Whether you choose to put on a blazer or not, this look will take you from happy hour with clients to date night in effortless style.

Chukka Boots with Dress Pants

Chukka Boots with Suit

The modern gentleman may want to style chukka boots with a suit for an elegant and bold look. For a casual suit outfit, you can wear suede or leather chukkas in black, dark brown, chestnut or cognac, depending on the cut and color of your formal wear. To start, make sure to avoid mixing deep brown footwear with black suits and textured suits with heavily napped suede shoes. Choose from timeless patterns and knits like tweed, herringbone, or houndstooth, and pair your suit with clean leather boots. Flannel trousers with a button-down shirt and suit jacket are perfect for dark suede footwear, while traditional black, navy, or grey suits should be dressed up with dark brown or black leather chukka boots. When putting on a tie, try matching the color to your boots.

Chukka Boots with Suit

Chukka Boots with Shorts

Practical and comfortable, guys can casually style chukka boots with shorts for a trendy urban look. Whether you’re camping or just walking around city streets, you can wear desert boots with matching cotton shorts and a front-tucked striped t-shirt.

Chukka Boots with Shorts

For a fun outfit perfect for music festivals or a summer lunch date, combine bright-colored shorts with a button-down and suede boots. For the perfect length, keep in mind that your shorts must stop just above your knee.

Chukka Boots with Men's Shorts

How To Wear Chukka Boots

  • You can wear chukka boots with jeans, chinos, dress pants, shorts and suits to create a stylish outfit.
  • Choose light colored chukka or desert boots for an effortless and relaxed look.
  • For a rugged and casual style, pair brown suede chukka boots with jeans and a fitted t-shirt or loose button-down shirt.
  • Dress up your leather chukkas with dark jeans, a dressy shirt, and a blazer for a smart casual outfit.
  • When styling a business casual outfit for work, combine quality pants with a butt-down collar dress shirt and cashmere sweater.
  • Always wear leather chukkas in dark shades such as black or dark brown for formal outfits.
  • Make sure to clean your suede chukka boots regularly to maintain the material and keep it looking nice.

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