Time To Start Thinking About the Best Men’s Chukka Boots for Fall

There’s something undeniably cool about chukka boots. With a silhouette that traces its roots back to desert escapades by the British military, the chukka boot remains an enduring and timeless menswear staple. Thanks to this easy-to-wear silhouette – plus functional leather uppers and, more often than not, a comfortable sole – the chukka boot is the most versatile pair of shoes you can pick up in late summer to carry you into fall. Don’t just take our word for it – see for yourself with our picks for the best men’s chukka boots.

Allen Edmonds Montauk Plain Toe Chukka Boots – $277
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Leave it to Allen Edmonds to take the traditional chukka boot and amp it up in a big way through the use of excellent suede and terrific construction. This is an understated-yet-premium pair of suede chukka boots, as ready to pair with light wash jeans and a short-sleeve henley as they are with olive chinos, a white Oxford, and a navy blazer.

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1901 Westport Chukka Boots – $54
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Available at a heck of a low price — perfect for back-to-school style no matter your age — this pair of grey chukka boots can lend surprising versatility to outfits made for hitting the books. Think dark denim and a white slub pocket tee and you’ll be the best-dressed guy in class.

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Florsheim Uptown Chukka Boots – $120
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Thanks to the right mix of affordability and style, we can’t get enough of the Uptown Chukka Boots. Done up in mocha suede, a  perfect shade to use to transition into early fall, these are the sleek chukkas you’re going to want to to the office or while traveling. We think they’re ideal when paired with charcoal chinos and a lightweight cotton crewneck sweater for seasonal transitions.

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Sperry Gold Cup Crepe Sole Chukka Boots – $154
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Although they boast an old-school silhouette and a comfortable crepe rubber in the sole, these boots don’t hint at their premium construction — that’s a good thing. The result is a go-anywhere style for August and on into early fall. We like ‘em best with slim, light khaki chinos and a navy linen-cotton cardigan for cool summer and early fall nights.

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Johnston and Murphy Copeland Chukka Boots – $159
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Falling on the more casual end of the spectrum thanks to the tan, oiled, full-grain leather, these durable chukkas embody what Johnston and Murphy does best: instant wearability and timeless style. The great thing about Copeland Chukka Boots is that they’d work with grey denim and a navy pocket tee on the weekend as seamlessly as with khaki chinos and a blue chambray shirt at the office.

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Nisolo Luca Chukka Boots – $198
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Seeking a pair of chukka boots that blend the rugged and the edgy? That’s the Nisolo Luca Chukka Boots, made with style and sustainability in mind. This is the right pair of chukka boots to wear to the office with slim indigo denim and a navy Oxford, and then keep on your feet for an evening rock show.

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