There’s no denying that the British have somewhat of a monopoly on being behind some of fashion’s most debonair and polished looks; chukka boots included. Chukka boots were first worn by British soldiers in World War II but quickly transcended into a popular footwear choice for men everywhere.
Today, the chukka boot is still extremely popular for its versatile smart-casual look that can easily elevate a simple white tee and jeans but can also blend perfectly with a shirt and tailored trousers at a formal affair. Typically made from leather or suede, every man should own at least one pair of chukka boots.
Features of a chukka boot
The best chukka boots are ankle-high, with rounded toes and open lacing with only two or three pairs of eyelets. They are usually made with premium leather or suede, although over the years many brands have produced contemporary versions with other materials.
Chukka Boot FAQs
What's the difference between a chukka boot and a desert boot?
A desert boot is actually a type of chukka boot. Traditional chukka boots have thin soles, whereas desert boots have a thicker spongy sole, but aside from that one difference, they are the same style of boot and are ultimately, both classified as chukka boots.
How do I style a chukka boot?
The beauty of the chukka boot is that they are extremely versatile and will go with pretty much everything in your closet. Pair chukka boots with jeans and a t-shirt for a relaxed look, or with chinos, a t-shirt, and an unbuttoned shirt for a cool smart-casual look.
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If you’re ready to add the versatile chukka boot to your footwear collection, we’ve rounded up the best chukka boots available that are stylish, durable, and comfortable, and are produced by some of the best footwear brands of all time.
Cole Haan has a small range of chukka boots that are part of their Original Grand collection. Featuring EVA midsoles with rubber outsole for added traction and durability, and their signature GRANDFØAM footbeds for luxurious cushioning and support, Cole Haan’s Chukka boots are a true blend of comfort and style.
Clarks’ range of chukka boots is rather large, and come in various materials and colours. Crafted from only premium leather or suede, Clarks’ chukka boots feature their signature crepe sole, and are extremely rugged and stylish.
The Grenson collection of men's chukka boots features several different handmade boots either crafted from suede or leather. All feature a classic rubber sole that’s chunky but lightweight and extremely comfortable to wear. Available in extremely sophisticated colours, any pair of Grenson’s chukka boots will elevate your wardrobe.
Astorflex has a collection of stylish, classic chukka boots with high-end Italian construction, made from healthy, eco-friendly leather and natural rubber, that are surprisingly affordable. Their chukka boots have all been handmade in Northern Italy by the same family for six generations, and are so comfortable you’ll feel like you’re walking on a cloud.
Nisolo have several styles of chukka boots available in a variety of stylish colours. Available in suede and leather, Nisolo’s chukka boots are no-nonsense boots made to suit the needs of any man on the go. Durable rubber soles provide the grip and traction needed to tackle any terrain, these boots are handmade sustainably & ethically, and will elevate any outfit you pair them with.
Their range of suede chukka boots, available in a variety of colours, are suitable for every occasion, and deliver Hudson’s signature craftsmanship that will make you look sophisticated and gentlemanly.
Base London has a huge range of men's chukka boots that have an extremely versatile boot silhouette. Regardless of the occasion, achieve a smart or casual look with a choice of high quality leather or suede uppers available in a variety of sole units and timeless colours.
Their range of chukka boots are definitely more casual than other brands featured in this guide, but are nonetheless stylish and comfortable. Made in the US from premium leathers and suedes, J. Crew’s chukka boots will become a staple in your wardrobe.
River Island has a great selection of chukka boots available in both suede and leather options, in a variety of timeless colours. Their chukka boots feature a classic, simple design that takes versatility to the next level; any pair of River Island chukka boots will become your new favourites.
Red Wing’s chukka boots are ankle-height lifestyle boots that balance flexible comfort with lasting durability. Each pair is built with deep archival inspiration and timeless style, and will make you look effortlessly polished no matter what outfit you pair them with.
Timberland has a huge range of chukka boots in classic, rugged, and contemporary designs. All have been crafted with premium leather, and most of Timberland’s chukka boots are completely waterproof. They all feature ultra-breathable OrthoLite foam insoles that provide moisture transport, antimicrobial function, and long-term cushioning, and are available in a great selection of neutral colours.
SeaVees have only one chukka boot to offer, but it does come in two colours. Made with Leather Working Group certified suede, and featuring a contoured, cushy foam footbed with extra heel-strike cushion for comfort, and SeaVees’ exclusive cooling system with perforations for breathability and cooling airflow channels, SeaVees’ chukka boot is an extremely stylish and comfortable option.
Joseph Cheaney & Sons
Traditionally designed, Joseph Cheaney & Sons’ chukka boots have a three-eyelet derby stacked on Goodyear welted soles for practicality, and are handcrafted at their Northamptonshire factory. With five colours available, Joseph Cheaney & Sons’ versatile chukka boots will fit any man’s wardrobe easily.
Ace Marks only have one chukka boot in their range, but it’s impeccably stylish and comfortable. Available in four colours, Ace Marks’ chukka boots have a supple calfskin leather construction, soft lining, and high ankle shaft for extra support and comfort. All handmade in Italy, a pair of Ace Marks’ chukka boots will add a touch of sophistication to any look with its distinctive style.
SOREL has a few chukka boots in their range that are all waterproof, lightweight, and contemporary in style. Crafted with either leather or suede, SOREL’s chukka boots are functional and refined; perfect for everyday wear and durable enough for even the hardest downpours of rain.
Using premium oiled Horween Chromepak leather and decades of leathercraft experience, Yuketen’s chukka boots are handmade in their Maine workshop and finished with a crepe sole. The crepe outsole provides superior shock absorption and a slip‐resistant tread, while the steel shank reinforcements form a stable bridge for even weight distribution. These American-made chukkas are extremely versatile; perfect for any and every occasion.
John Lewis & Partners
John Lewis & Partners has a huge range of men’s chukka boots, all of which are a refined smart-casual choice of footwear. Their selection includes a variety of colours, in both leather and suede. Whether you prefer a more hardwearing, durable chukka boot, or a smart and sophisticated chukka suitable for formal occasions, John Lewis & Partners will have the perfect pair for you.
Allen Edmonds has a fantastic collection of men’s chukka boots, in various styles and colours. All are made with premium leather or suede, and will give you an elevated casual style; perfect any way you wear it. Allen Edmonds have both innovative, modern chukkas and traditional, timeless chukka boots, so no matter what you’re looking for in a chukka boot, Allen Edmonds will have it.
Their range of chukka boots is small but mighty; they craft their chukka boots from premium materials, including rich leathers and suedes, for boots that’ll stand the test of time while maintaining the classic, refined look Brooks Brothers is known for.
Steve Madden’s chukka boots are made with rich leather and will add a rustic charm to your look. Perfect for any occasion, any pair of Steve Madden chukka boots will become your new go-to, as they are the perfect combination of street-style cool and formal sophistication.
Their range of Chukka boots is small but mighty. Crafted with premium leather, TAFT’s chukka boots are a perfect blend between traditional and contemporary. TAFT chukka boots will definitely make you stand out in a crowd.
Their range of chukka boots are crafted with premium full grain leather, and are available in multiple styles and colours.
Allbirds has a rather modern and casual version of the chukka boot. Water repellent and odour minimising, Allbirds’ chukka is made with renewable wool and is so flexible that the boot will conform to your feet and movements. Stylish, comfortable, and sustainable? Yes, please!