5 of the Best Chukka Boots for Men

Boots come in all shapes and sizes but when you’re looking for something that is both stylish and comfortable, Chukka boots are probably our top pick here at Coolector HQ. There is no shortage of options when finding the perfect pair of Chukkas and regardless of your sense of style and budget, you’re sure to find something that fits the bill in our round up. The versatility and effortless cool of Chukka boots differentiates them from the competition and if you’re after a new pair this autumn and winter, you’re in luck.

Check out our pick of 5 of the best Chukka boots for men below:

Lems Boulder Chukka Boots – $120

Classy and devilishly dapper, these Lems Boulder Chukka Boots ($120) boast a supremely comfortable suede upper that gives them an effortlessly cool aesthetic. Comfort and style are two key components we’ve come to expect from all Lems Shoes and, as you would expert, their new Boulder Chukka is no different. Like a chukka should be, the Boulder can be dressed up or down while providing a cool, straightforward design that matches with anything in your wardrobe. 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 – $150

Another supremely cool piece of footwear, these Nisolo Emilio Chukka Boots ($150) are definitely right up our stylistic street here at Coolector HQ. Nisolo’s line of refined classics are about as good as it gets as far as we’re concerned. Their Emilio Chukka is a dapper take on the classic chukka silhouette, and it a should be a style staple for your wardrobe this autumn and winter. Everything that you’ll have loved about the original Emilio boots from Nisolo – such as the versatility of wearing options and thoughtful craftsmanship – remains the same, but they have upgraded it with a rugged waxed leather upper. They look just as great with cuffed jeans and your favorite tee as they do with chinos and a sport coat. ($150)

Rhodes Dylan Chukka Boots – $150

Desert boots are all about durability, comfort, and rugged good looks and these awesome Rhodes Dylan Chukka Boots ($150) excel in all three areas. Every feature of these boots was carefully considered to craft an everyday desert boot that can do any job, and do it well. Handmade in Italy, these brilliant boots boast Rhodes’ signature craftsmanship and only the highest-quality materials for an essential addition to the contemporary man’s wardrobe. The soft, supple Italian leather upper is unlined for lightweight comfort, and the 100% natural rubber sole is like walking on a cloud. We’d wear these boots everyday if we could, and know you’ll want to, too—they’re that ridiculously comfortable and stylish. ($150)

Astorflex Greenflex Chukka Boots – $165

Definitely one of our favourites on the list, these Astorflex Greenflex Chukka Boots ($165) boast the sort of style favoured by WWII desert soldiers and icons like Steve McQueen. They have an environmentally responsible construction and they are, quite simply, one of the best kept secrets in men’s footwear. Handmade in Northern Italy by a family that’s been making boots for six generations, these boots are eco-friendly, supremely stylish, and represent the best value on the market. It all starts with premium European leather that’s aged for 30 days in an all-natural mixture of water, oak bark, and powdered mimosa. The leather is then softened with all-natural ingredients to produce a leather that is supple and environmentally friendly. The boot is then finished with 100% natural rubber soles that feel like walking on a cloud. ($165)

Redwing Heritage Weekend Chukka Boots – $230

Crafted from full-grain roughout leather from S.B. Foot Tanning leather, a Red Wing owned-and-operated tanning company based in Red Wing, Minnesota, these first class Weekend Chukka Boots ($230) are going to tick your style and comfort boxes. Red Wing Heritage, manufacturer of high-quality leather work boots boasting more than 100 years of experience, departs from their traditional occupation-specific designs with a casual off-the-clock shoe. Made with Red Wing’s traditional construction methods and materials, the Weekender Chukka is flexible, lightweight and exceptionally wearable right out of the box. They offer a stitchdown construction allows for resoling when necessary, extending the life of the boots and have ComfortForce® footbed for a relaxed ride and all-day comfort. ($230)

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