10 of the best chukka boots for men

So far as classy footwear is concerned, chukka boots are mighty tough to beat and, as is always the case when we’re after new footwear, Huckberry is one of our first ports of call. If you fancy some classy footwear for your autumn / winter adventures, read on. Check out our pick of 10 of the best chukka boots for men below:

AstorFlex Greenflex Chukka Boots – $165

An eco-friendly Desert boot, handmade in Italy and available exclusively at Huckberry, what’s not to like about the AstorFlex Greenflex Chukka Boots ($165). Offering the sort of style favoured by WWII desert soldiers and icons like Steve McQueen, these boots are as classy as they come. Made from a soft, supple nubuck leather from Europe that ages beautifully and the 100% natural rubber soles feel like walking on a cloud. ($165)


Rhodes Felix Chukka Boots – $168

The Felix Chukka Boots from Rhodes ($168) are made to last and built for comfort. Each feature was carefully considered to craft an everyday chukka that can do any job, and do it well – these will be the footwear you reach for whatever the occasion. Boasting a Texon® insole with thermal insulation and anti-shock foam layer provides all-day comfort and each pair is handcrafted in Portugal by experienced bootmakers using expert methods and techniques to ensure lasting quality. ($168)


Red Wing Heritage Weekender Chukka Boots – $219

Made from full-grain oil-tanned leather from S.B. Foot Tanning leather, a Red Wing owned-and-operated tanning company based in Red Wing, Minnesota, these Weekender Chukka Boots ($219) have a quality that is second to none. They have a stitchdown construction that allows for resoling when necessary, extending the life of the boots considerably. They are crafted from water, stain and perspiration resistant premium leather for an unparalleled performance day in, day out. ($219)


OluKai Hawaiiloa Manu Ihu Chukka Boots – $150

Named after the great, historic Hawaiian voyaging canoe, the Hawai’Ilao Manu Ihu’s are Olukai’s latest in terrain-tested footwear and a super classy pair of chukka boots. These relaxed shoes are a nod to the classic chukka silhouette, only with the supreme comfort and rugged toughness that only Olukai can bring to the table. Great for any adventure they’re a time-tested shoe that adds robustness and style to your wardrobe rotation. ($150)


Adelante Shoe Co Santiago Chukka Boots – $245

The nubuck leather Santiago chukka boot from Adelante Shoe Co ($245) are made from premium materials by well-paid craftsmen. They have a Goodyear welted construction is durable and fully resoleable and the high density memory foam insoles provides all-day comfort. For every pair sold, a care package is dropped off to craftsmen in Pastores, Guatemala who are currently unemployed due to COVID-19. Every pair is proudly handcrafted in Guatemala by a skilled craftsman who is paid over the Living Well Line, a standard developed by balancing World Bank data with individual interviews to define the wages needed to live well in a specific location. ($245)


Lems Boulder Chukka Boots – $120

Comfort and style are two key attributes we’ve come to expect from all Lems Shoes and their new Boulder Chukka Boots ($120) are certainly no exception. Like a chukka should be, the Boulder can be dressed up or down while delivering a stylish, understated design that matches with anything in your closet. While on the comfort side, Lems included their iconic IBR outsole and lightweight flexibility for a complete chukka that you’ll lean on day in and day out. ($120)


Nisolo Emilio Chukka Boots – $160

The Emilio Chukka from Nisolo ($160) take their design inspiration from the traditional chukka boot but the twist is in the sleek leather sole. They have built-in arch support, a classy yet robust leather outsole and Nisolo have added a layer of stitching between upper and leather sole for a slightly more rustic aesthetic that we’re loving here at Coolector HQ. ($160)


SeaVees Huntingdon Chukka Boots – $91

Boasting a soft suede upper which is ridiculously soft and easy to wear right out of the box, these SeaVees Huntingdon Chukka Boots ($91) are versatility personified. They have an inner elastic gore for easy on and easy off and a custom perforated footbed offers extra cushion and comfort. The Huntington Chukka is a new type of slip on with a mid-rise upper that captures the quintessential surf style – contemporary, no-nonsense and supremely comfortable. ($91)


Helm Declan Chukka Boots – $236

Boasting a classic and timeless chukka silhouette which can be effortlessly worn for causal and formal settings alike, these Helm Declan Chukka Boots ($236) has a timeless aesthetic that will be a mainstay of your wardrobe rotation. With an upper crafted from a premium, full-grain Balthazar leather that’s supple out of the box and the Helm signature white composite rubber midsole delivers cushion and style that is specific to Helm Boots. ($236)


Rancourt & Co Acadia Chukka Boots – $238

This classic moc-toe chukka boasts a look that Rancourt has mastered over decades of experience and the Acadia Chukka ($238) is one of their finest to date. The upper is crafted from a unique and highly robust textured bison leather sourced from Tasman Tannery in Maine. They are unlined for a comfortable feel in any weather – a feature which also aids in the quick break-in process. ($238)

Leo is the owner of The Coolector and writes about the stuff he loves. And some stuff that he merely likes.