With the possible exception of slipping on a perfectly fitted suit, in the world of menswear there are few feelings as satisfying as sliding your foot into a stylish pair of chukka boots.
Chukkas, also called desert boots – though that’s technically a specific subset of chukkas – strike a perfect balance between masculinity and comfort.
While they get their name from the sport of polo (a chukka in polo is kind of like an inning in baseball), they gained popularity in the mid-20th century after men brought them home from the Second World War, and were cemented as staples of menswear (at least in my mind) after Steve McQueen roguishly rocked them in the 1960s.
Today they’re the perfect way to inject a bit of ruggedness into an otherwise refined look, without sacrificing any style. And fortunately, you don’t have to look very far to find a well made, stylish pair that you can wear the hell out of.
In this post I’ve rounded up 17 of the best men’s chukka boots available to buy online, each of which will help you channel the King of Cool.
The Best Men’s Chukka Boots on Amazon
Thursday Boot Company
$149 | Scout Men’s Chukka Boot
JOUSEN
$36 | Classic Suede Desert Boot
Clarks
From $37 | Men’s Bushacre 2 Chukka Boot
BRUNO MARC NEW YORK
From $21 | Original Suede Leather Desert Storm Chukka Boots
London Fog
From $23 | Mens Broadstreet Chukka Boot
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Mark Nason
From $70 | Los Angeles Men’s Weldon Chukka Boot
ECCO
$299 | Men’s Turn Chukka Boot
FRYE
$179 | Men’s James Bal LE Boot
Timberland
From $59 | Men’s EK Brook Park Chukka Boot
GM GOLAIMAN
$39 | Genuine Suede Chukka Boots
Cole Haan
$158 | Men’s Glenn Chukka Boot
Dunham
From $57 | Men’s Gavin-dun Chukka Boot
Madden
From $49 | Men’s M-Dodge Chukka Boot
Florsheim
From $72 | Men’s Spark Chukka Boot
Johnston & Murphy
$159 | Men’s Copeland Chukka Boot
Ferro Aldo
$39 | Sterling MFA606325 Mens Casual Chukka Slip on
Rockport
From $33 | Men’s Classic Break Chukka Boot
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Further Reading:
- The Best Men’s Shoes – Irreverent Gent
- Style Icon Steve McQueen – Irreverent Gent
- What to Wear in the Fall – Irreverent Gent
- The Best Men’s Shoes for Plantar Fasciitis – Irreverent Gent
- The 25 Best Men’s Shoes for Standing All (Damn!) Day – Irreverent Gent
- The (Absolute) Best Men’s Casual Shoes – Irreverent Gent
- 10 Best Chukka Boots For Men – Gear Moose
- The Best Chukka Boots Guide You’ll Ever Read – Fashion Beans
Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a (patient, if long-suffering) Toronto sports fan and the husband of a wonderful (and fortunately much more patient) wife.