8 Chukka Boots As Sturdy As They Are Stylish

It's the question that faces every guy when he gets dressed in the morning: Form or fuction? Well, contrary to everything you may have ever known, it's eminently possible to have both. Just slip into a chukka boot—the only thing in a guy's closet that can put up with the elements and turn heads in equal measure.

Brooks Brothers Unstructured Suede Chukka Boots photo

1 of 8

Brooks Brothers Unstructured Suede Chukka Boots

These suede chukka boots, which come in perhaps the world's richest shade of brown, can be dressed up or down. For a great mid-fall transition piece, you'd be hard-pressed to do better than this. ($548; brooksbrothers.com)

Buy these Brooks Brothers chukka boots now
Paul Evans The Newman Chukka Boot photo

2 of 8

Paul Evans the Newman Chukka Boot

Made from certified Italian leather (meaning: it's the real deal, since Italian law prohibits companies from using that phrase unless it's genuine Italian leather), these handsome burnished beauties are as dressy as chukkas get. You'll want to reserve them for only the most decadent affairs. ($500; paulevansny.com)

Buy these Paul Evans chukka Boots
Fratelli Giacometti Burnished Leather Chukka Boots photo

3 of 8

Fratelli Giacometti Burnished Leather Chukka Boots

Starring a luxurious patina and hand-stiched welts, few shoes on the market are constructed with this level of attention-to-detail. Though they're technically boots, you might want to keep these tucked away inside—safely ensconed in shoe bags, of course—during fall's worst weather. ($1,115; barneys.com)

Buy these Fratelli Giamometti chukka boots now
John Lobb Grove Suede Chukka Boots photo

4 of 8

John Lobb Grove Suede Chukka Boots

The soft suede shoe—hand-crafted by premier British footwear company John Lobb—features a comfortable and durable rubber sole that will hold up well through the season. For maximum wintry cool effect, pair with a chunky brown overcoat. ($1,465; mr.porter.com)

Buy these John Lobb chukka boots now
John Varvatos Star USA Seagher Suede Chukka Boot photo

5 of 8

John Varvatos Star USA Seagher Suede Chukka Boot

For an added cowboy-cool effect, look no further than these suede chukkas from John Varvatos. Soft tan suede and an upturned toe give the ultimate modern Wild West look. It's the perfect shoe for a casual fall evening. ($268; bloomingdales.com)

Buy These John Varvatos Boots Now
Crockett & Jones Hartland 2 Leather Chukka Boot photo

6 of 8

Crockett & Jones Hartland 2 Leather Chukka Boot

Turn heads with these Crockett & Jones handcrafted chukka boots. They're made of grained leather, giving them a unique look, and the light brown color makes these boots suitable for any summer occasion. ($650; barneys.com)

Buy These Crockett & Jones Boots Now
Vince Men's Brunswick Suede Chukka Boot photo

7 of 8

Vince Men's Brunswick Suede Chukka Boot

Available in two sumptuous tones (a light beige, and a chocolate brown, which we're more fond of), this Vince chukka is more than meets the eye. On the outside, you'll find butter-soft suede—but the insoles are lined with it, too, for an ultra-comfortable fit. ($350; neimanmarcus.com)

Buy These Vince Boots Now
To Boot Derby Cognac photo

8 of 8

To Boot Derby Cognac

As sleek as a Formula One car (and as pretty as one, too), these cognac leather chukka boots are sure to impress any crowd. For maximum effect, pair them with a deep blue suit. ($495; toboot.com)

Buy these To Boot New York chukka boots now