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.
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.
Why Trust Us?
- We’ve selected brands that have a history of making high-quality men’s chukka boots
- These brands display great design and modern styles
- At a price point that we think is reasonable.
- We have over 12 years of producing men’s fashion advice and product recommendations
If you’re ready to add versatile chukka boots 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
1/16
Price: From $180
Sizes: 7-16
Material: Leather
Founded in 1928, in Chicago, Cole Haan is an American brand renowned for its footwear which is both aesthetically-pleasing and functional. Cole Haan employs various technologies when crafting its footwear, to ensure ultimate comfort, most notably the Zerogrand, and Original Grand collections.
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
2/16
British company, Clarks, may invoke a flashback to schoolyard days and handball courts, but trust us, Clarks makes comfortable and stylish shoes for adults too (even though you most likely know the brand for their ‘school shoes’).
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.
Astorflex
3/16
Founded in the 19th century, Astorflex has a rich heritage. Produced entirely in Italy, Astorflex takes a responsible, sustainable approach to its laid-back footwear. Their desert boots are even described by some as “the best desert boots in the world”.
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
4/16
Premium footwear brand, Nisolo has a very clear vision: ‘to push the fashion industry in a more sustainable direction – where success is based on more than just offering the cheapest price – a direction that not only values exceptional design, but the producer and the planet just as much as the end consumer’. And they easily achieve this with their stylish shoes that are fairly priced and sustainably made.
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.
Base London
5/16
Established in 1995 to tend to the footwear demands of the British male, Base London has grown into a globally known premium shoe brand. Using only the finest quality leathers combined with their excellent craftsmanship, Base London always has a perfectly formed range of fashion focused formals, versatile semi-formals, and comfortable casual styles, season after season.
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.
River Island
6/16
At River Island, great design is at the heart of everything they create. Founded in 1948, the UK brand is one of the best known on the High Street, and prides itself on producing stylish yet affordable fashion. Catering to men, women, and kids, River Island also sells exquisite footwear and accessories.
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
7/16
The Red Wing Shoe Company has a clear but simple purpose: to be a great company that makes a difference in people’s lives. Fueled by strong values and a commitment to fine craftsmanship (that has been at their core for over 100 years) allows Red Wing to produce nothing but stylish, durable, and comfortable footwear.
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
8/16
Famous for their original waterproof boots, for which the brand was named after, Timberland continues to remain loyal to their company values: hard work, innovation, and a love of the great outdoors. They do so by producing high-quality, durable, comfortable, and stylish shoes that can be worn in any kind of weather.
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
9/16
Founded in 1964, SeaVees produces footwear with the comfort of a sneaker but the sophistication of dressier shoes. Their shoes are carefully crafted in small batches to control quality and consistency, and are only made with premium textiles and the finest leathers.
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
10/16
Founded in 1886, the team behind premium footwear brand Joseph Cheaney & Sons are committed to continuing the production of high quality shoes entirely made in Northamptonshire, England, from the cutting out of the leather to the final polishing; just as it was in the 1800s.
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.
SOREL
11/16
Founded in 1962, SOREL combines expert craftsmanship and of-the-moment design to create all-season footwear. What began decades ago with premium boots, crafted with an unparalleled balance of construction and protection, is now a brand dedicated to both functionality and fashion. SOREL challenges the status quo by creating unexpected footwear that pushes the boundaries of function-first fashion.
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.
Allen Edmonds
12/16
Founded in 1922, Allen Edmonds is a premium men’s footwear and accessories brand. Since their inception, Allen Edmonds have been creating timeless, stylish, and comfortable men’s dress shoes and casual shoes using only premium leathers.
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.
Brooks Brothers
13/16
The oldest clothing and footwear retailer in the US, is also still one of the best. Founded over 200 years ago, Brooks Brothers has been an outfitter of choice for virtually all the US Presidents, as well as a number of America’s elite regiments.
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.
TAFT
14/16
Founded in 2014, TAFT is a men’s footwear brand specialising in unique, bold shoe designs. TAFT shoes are produced in Spain and Portugal with premium textiles ranging from suiting wool, to woven upholstery fabric, to Charles F. Stead leather. Meticulous in their work, intentional in their designs, and obsessive over what makes the cut, TAFT has become well-known for their extremely well-made unique men’s shoes.
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.
Beckett Simonon
15/16
Beckett Simonon, founded in 2011, believes in the power of well-made products which make you look and feel your best; products you can wear year after year, and repair rather than replace. Which is why they produce stylish high quality shoes, available for unrivaled prices and made with responsible manufacturing processes.
Their range of chukka boots are crafted with premium full grain leather, and are available in multiple styles and colours.
Allbirds
16/16
New Zealand-American company, Allbirds is dedicated to creating eco-friendly footwear made from sustainable resources, but that doesn’t mean that Allbirds’ sneakers don’t deliver in the comfort or style department.
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!
