Chukka Boots

Astorflex Brownflex chukka boot


Chukka Boots

A price and style comparison

When it comes to classic footwear that every man should have in his closet, a pair of chukka boots definitely tops the list. Because it's something of a secret weapon shoe—it has the ability to add a nice contrast to whatever it is you're wearing. Pair them with your beat-up jeans or worn-in cotton chinos and let them give your dress pants a shot of relaxed cool. It's at once classic and current.

But who makes the best ones? And how much should you spend? That's a matter of personal taste and budget. We pulled on several different styles to put together this three-tier recommendation. Whether you need a reliable starter pair or are prepared to lay down twice as much for a pair that can be repaired and resoled over and over again, these are the suede chukkas that won't let you down.



OG Pair

• Made in Vietnam

• Metal grommet eyelets and sturdy cotton laces

• Cushioned insole provides extra comfort

• No interior lining and the sole is lighter in weight

Suede desert boot,
$150 by Clarks


Continental Pair

• Made in Italy

• Full leather lining delivers all-day comfort and more structure than a standard chukka

• The ergonomic leather footbed conforms to the shape of your foot

• 100% natural crepe rubber is surprisingly durable

Brownflex chukka boot,
$215 by Astorflex


Refined Pair

• Made in England

• Built on a custom last for a more traditional shoe shape, with a slight rise in the arch

• Full calf leather lining provides extra comfort and a pull tab at the heel makes it easy to put on

• The crepe rubber sole is Goodyear welted

Bertie chukka boot,
$300 by Sanders

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