6 of the best chukka boots for men in 2021

Of all the different sorts of men’s boots out there, chukka boots are amongst our favourites here at The Coolector and there are plenty of different ones to choose from to suit every style and budget. If you find yourself in the market for a new pair of men’s chukka boots this year, you’re going to want to check out our pick of 6 of the best below:


AstorFlex Greenflex Chukka Boots | $195

The Greenflex chukka boot from AstorFlex is 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 great looking boots are eco-friendly, handsome as hell, 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. Comfort and style rolled into one.


Adelante Shoe Co. Santiago Chukka Boots | $260

This nubuck leather chukka boot is made from premium materials by well-paid craftsmen and boasts the traditional elastic panels and pull tab for easy on-off and unmistakable style. The high density memory foam insoles provide all-day comfort and every pair sold funds a care package dropped off to craftsmen in Pastores, Guatemala who are currently unemployed due to COVID-19.


Red Wing Heritage Weekender Chukka | $230

Red Wing Heritage, manufacturer of high-quality leather work boots boasting more than 100 years of experience, departs from their normal occupation-specific designs with a casual off-the-clock shoe that we’re loving here at Coolector HQ. The Weekender Chukka is made with Red Wing’s traditional construction methods and materials, making them flexible, lightweight and exceptionally wearable. 


Rhodes Tyler Chukka Boots | $175

Boasting an everyday chukka silhouette elevated with custom-developed last for a refined shape, these are about as classy as they come. The Rhodes Tyler Chukka Boots are made from a waxy leather that takes on a personalised patina over time and each pair is made in Leon, Mexico, the heart of Mexico’s shoe industry, where experienced bootmakers use proven methods and materials to ensure top quality.


Nisolo Cusco Travel Chukka | $80

With an eye on far off locales, Nisolo named the Cusco Travel Chukka Boots for the Peruvian destination and built the boots with everything you could want in a travel companion. Packable, water-resistant, and delivering unparalleled comfort, these great boots will have you ready to map out your next adventure, keeping your feet very happy in the meantime.


Lems Boulder Chukka Boots | $135

While the robustness, lightweight feel, and zero-drop experience of the Boulder Boot has remained the same, Lems have come up with the Boulder Boot Mid as a lighter mid-sized version of their bestselling boot. Courtesy of the hyper packability, these are the easiest boots to travel with—no seriously, you can roll them up and stuff them anywhere. Built for life in the outdoors but designed for your everyday adventures, there’s no place the Boulder Boot Mid can’t go.


Leo Davie
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