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.
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
1/24Price: From $180
Sizes: 7-16
Material: Leather
Customer Reviews: “This is my 3rd pair of these chukka boots that’s how much I love them. They are the best pair of shoes I have ever worn. I am in the go a lot and I’m a big and tall fella so I change them out yearly. The last pair and this one I had to get on the waiting list for them.”
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
2/24Price: From $200
Sizes: 6-12
Material: Leather
Customer Reviews: “Excellent quality and great price. Clarks have a great reputation and didn’t disappoint.”
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.
Grenson
3/24Price: From $505
Sizes: 6-12
Material: Natural-grain calf leather
Customer Reviews: “Very handsome boot with quality construction and materials.”
Founded in 1866, Grenson has been continuously making durable and high-quality shoes. All of Grenson’s shoes are ‘Goodyear Welted’, a shoemaking technique, meaning the shoes are very strong and will last for a very long time.
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
4/24Price: From $195
Sizes: 7-15
Material: Premium leather
Customer Reviews: “too early to say how comfortable they are as I just got them, however, the color of the shoe not too light nor dark just how I like it, overall impression – very cool.”
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
5/24Price: From $180
Sizes: 8-13
Material: Waterproof leather
Customer Reviews: “First off the smell is absolutely wonderful, and even now my room still smells of them. They’ve been breaking in very nicely and I’m excited to watch the patina form over time!”
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.
Hudson
6/24Price: From $250
Sizes: 7-13
Material: Leather
Customer Reviews: “They are comfortable and stylish with both jeans and khakis, and I often get comments about these shoes.”
Founded in East London in 1990, Hudson Shoes was created with the aim of providing premium, contemporary footwear for the modern man.
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
7/24Price: From $98
Sizes: 5-12
Material: Premium leather
Customer Reviews: “Nice-looking boots with sturdy soles and smooth leather upper.”
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.
J. Crew
8/24Price: From $158
Sizes: 7-13
Material: Italian suede
Customer Reviews: “Public Service Announcement: these are simply the finest desert boots one can buy. Italian craftsmanship that exceeds expectations. The MacAlisters are incredibly well made and have a sleek silhouette that manages to be both modern and timeless.”
J. Crew believes in ‘looking a million bucks, not spending it’ which is why they source the best high-quality fabrics at the most accessible prices. All of their products are classic with a modern twist, meaning you’ll always look effortlessly polished when sporting J. Crew.
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
9/24Price: From $87
Sizes: 7-13
Material: Faux leather
Customer Reviews: “Great boots on a good deal… Really happy with these boots they look trendy and very comfy and the price I will order another pair.”
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
10/24Price: From $249
Sizes: 7-13
Material: Nubuck leather
Customer Reviews: “Brought these about a year ago from the factory store in Red Wing, could not be happier very comfortable and well built.”
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
11/24Price: From $100
Sizes: 7-15
Material: Better leather
Customer Reviews: “These shoe are very comfortable, they get dirty easily but they are very stylish!”
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
12/24Price: From $140
Sizes: 7-13
Material: Leather, organic cotton
Customer Reviews: “These shoe are very comfortable, they get dirty easily but they are very stylish!”
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
13/24Price: From $440
Sizes: 6-12
Material: Leather
Customer Reviews: “These are my second pair of Jackie Chukka boots. As the world has moved to more casual business attire these boots complement chinos and a smart shirt perfectly. Big thanks to Carina in Bow Lane for her ongoing support and enthusiasm!”
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.
Ace Marks
14/24Price: From $350
Sizes: 5-15
Material: Full-grain Italian calf skin leather
Customer Reviews: “This was my first pair of ACE MARKS Chukka’s. Following the sizing guide, my new CHUKKA’S fit “like a glove”! I would highly recommend this boot to all!”
Ace Marks is dedicated to producing reasonably priced, cleverly contemporary, utterly luxurious and comfortable dress shoes that make a lavish powerful statement. Founded in 2016, Ace Marks’ believes you shouldn’t have to spend obscene amounts for a handcrafted world-class shoe, which is why their luxurious men’s shoes are fairly priced.
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
15/24Price: From $135
Sizes: 7-15
Material: Full grain leather
Customer Reviews: “Definitely…comfortable & lightweight! I got these boots to replace some chunkier waterproof boots and they really hit the spot.”
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.
Yuketen
16/24Price: From $572
Sizes: 8-13
Material: Horween chromepak leather
Customer Reviews: “I am blown away by the quality of these shoes. The stitching is sturdy, and you can definitely feel the heft of the Yuketen construction that they describe on their website. The leather is between 1/16 and 1/8″ thick, has a consistent, thick nap and is soft and smooth on the inside”
Using traditional shoe-making techniques and heritage styles as their foundation, Yuketen produces reimagined shoes; by adding here and taking away there, the result is modern hybrids of all the best-looking and comfiest parts.
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
17/24Price: From $65
Sizes: 7-12
Material: Leather
Customer Reviews: “Boots are comfortable, pleased with style and seem to be weatherproof.”
John Lewis & Partners go above and beyond to offer quality products and outstanding service. Based in the UK, John Lewis & Partners is committed to inspiring and delighting their customers through their high quality clothing, footwear, beauty, and homeware products.
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
18/24Price: From $375
Sizes: 7-14
Material: Leather
Customer Reviews: “Boots are comfortable, pleased with style and seem to be weatherproof.”
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
19/24Price: From $265
Sizes: 8-13
Material: 100% Leather
Customer Reviews: “These are excellent casual shoes / boots. Where them constantly – very comfortable and come with leather shoe laces.”
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.
Steve Madden
20/24One of the most iconic brands in footwear, Steve Madden has revolutionized the shoe industry, merging years of experience with unique and creative designs. Dedicated to producing products that are authentic and embrace individuality, there’s no surprise why Steve Madden designs have been propelled to the forefront of fashion.
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.
TAFT
21/24Price: From $350
Sizes: 6-15
Material: Woven Italian leather
Customer Reviews: “This makes 19 pairs of Taft in about 18 months as I just found out about this super cool brand!”
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
22/24Price: From $239
Sizes: 7-14
Material: Full-grain calfskin leather
Customer Reviews: “A well made pair of sturdy boots suitable for the office or a night out. This is my second pair of footwear from Beckett Simonon and it will not be my last.”
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
23/24Price: From $145
Sizes: 8-14
Material: ZQ Merino wool
Customer Reviews: “These shoes are just about perfect for California winter. They’re warm, sturdy, and offer both support and the comfort that I’ve come to associate with the Allbirds line. Definitely happy to have made the purchase.”
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!
Veldskoen
24/24Price: From $180
Sizes: 3-15
Material: Leather, 100% recyclable rubber
Customer Reviews: “Just purchased them. Truly truly comfortable. I also keep getting compliments on them by people in Seattle where I live. I think I will buy a second pair in a different color.”
All of Veldskoen’s shoes are handcrafted in South Africa with locally sourced, premium materials. The brand is committed to crafting shoes that are not only ethically and responsibly made but, feel crazy comfy and provide effortless daily style.
Veldskoen has a small but mighty range of Chukka boots that are extremely stylish and well-made.
