5 Pairs Of Chukka Boots To Have You Lookin Fresh AF This Fall

best men's chukka boots

Chukka Boots should be a staple in every man’s shoe collection. These boots are a timeless design with the same repeating elements throughout which include an ankle-high design, suede or leather upper, leather or rubber sole, open lacing, 2 or 3 eyelets (usually).

With Autumn on the horizon I thought I’d throw out some stylish Chukka boots, ranging in price, for you bros to choose from. Scoop up your favorite today and get that ‘fit right before Fall kicks into full gear. On the top left, we see the Lems Shoes Boulder Chukka in Lion’s Mane which has a moisture-wicking PU insole and unlike the others in this roundup, it’s designed so you can roll the shoe up for easy packing. This makes it a perfect travel shoe for anyone out there who spends a lot of time on the road.

In the top center, we’ve got the Nisolo Emilio Chukka Boot (SALE) which is handmade in Peru and features a full-length soft sheep leather insole that’s extremely comfortable. It has excellent built-in arch support, a slip-free rubber heel cap, and the stitching is reinforced throughout so they’ll last longer. Over on the top right, the Astorflex Greenflex in Dark Brown Nubuck are handmade in Northern Italy by a family that’s been handmaking shoes for SIX generations. This is designed in the style of WWII desert soldiers and fashion icon Steve McQueen. The 100% natural rubber soles give you an effortless glide so you can stand and walk all day in comfort.

On the bottom left, the Rhodes Footwear Felix Chukka is handcrafted in Portugal by some of the most experienced bootmakers on the planet. If you’re a regular reader of BroBible’s Style and Gear coverage then you already know I have a soft spot for Portuguese products because they’re typically a cut above the rest in terms of quality and craftsmanship. In these shoes, the Texon® insole with thermal insulation and anti-shock foam layer provides all-day comfort.

Last up, on the bottom right we’ve got the Red Wing Heritage Weekender Chukka which are handmade from a full-grain roughout leather that’s been sourced from the S.B. Foot Training tannery, a leather tanning company that’s owned by Red Wing Heritage and based in Red Wing, Minnesota. These chukka boots are made in the USA (obviously) and the ComfortForce® footbed is unrivaled in comfort. This premium leather is stain, water, and sweat-resistant.

Let’s check out today’s boots again:

best men's chukka boots

[1] Lems Shoes Boulder Chukka in Lion’s Mane [$120]

[2] Nisolo Emilio Chukka Boot (SALE) [$150]

[3] Astorflex Greenflex in Dark Brown Nubuck [$165]

[4] Rhodes Footwear Felix Chukka [$198]

[5] Red Wing Heritage Weekender Chukka [$230]

Are you looking for other styles of boots? You can check out this roundup of the Best Waterproof Boots For Men or this collection of the 14 Best Hiking Boots For Men.

By the way, if you know of a product that should be featured here you can hit me up on email at cass@brobible.com, or find me on Twitter at @casspa. Or if you’ve got an idea for a daily theme I should touch on then hit me up!


The BroBible team writes about gear that we think you want. Occasionally, we write about items that are a part of one of our affiliate partnerships and we will get a percentage of the revenue from sales.