The 5 Best Chukka Boots You Can Wear With Shorts

Snugly nestled in the spot between work boot and dress shoe, the chukka is the perfect shoe when you can’t decide between dressy or casual. Plus, it’s the only boot you can wear with shorts. (Never forget this. If I see another pair of Iron Rangers with denim cutoffs I’m going to lose it.)

Because it straddles that fine line between shorts and slacks it’s tough to land on the right chukka. Too formal and it’s unwearable with summer outfits. Here I’ve landed on some of the most interesting, innovative, chukka boots on the market.

[Related: Chukka vs Chelsea – Which Is Right for You?]

1. Clark’s – Desert Boot

The original. This may be the most popular chukka boot and the reason is that it does informal well. Most options are in suede of varying quality and the price can be anywhere between $90 and $190 for a pair. The crepe sole won’t last long and they get super dirty, but man are they comfy.

See my review of the Clarks Desert Boot or shop different styles here

red wing chukka

2. Red Wing Heritage Men’s Chukka

A lot of guys wonder why one would spend $260 on casual boots, but the cool thing about these chukkas is they’re available in the same super high quality, full grain leather you can get for your Iron Rangers. Look at a pair of these and you’ll think less of Desert shoes and more of deck shoes: they’ll get approving nods at country clubs.

Browse 5 kinds of Red Wings Chukkas here.

Bruno Marc chukka

3. Bruno Marc New York Desert Storm Chukka

Twenty-five dollar chukkas? Twenty-five dollar chukkas. Sure, the suede is probably split-hide, the color might be a little inconsistent, and it’s a glued on sole but you’ll probably get a season out of these decent looking shoes and if you’re unsure about chukkas in general, it’s a safe bet.

See more styles here.


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4. Allen Edmonds Dundee 2.0

Light, comfortable and with great arch support, these will look a little off when paired with a summery beach outfit but with khaki shorts and a short sleeved button down they work just fine. The leather kind are over $300 but it’s not too hard to find suede on sale for under $200.

Browse Chukkas on Allen Edmond’s site.

5. Thursday Boot Company – Scout

Thursday’s is known for inexpensive footwear and while their chukkas aren’t as cheap as Clark’s, they’re head and shoulders above them in quality. Available in several suedes as well as full grain leather, many options are Goodyear welted and leather lined. Available in rubber soles or a good old fashioned crepe, it’s the perfect middle ground between Clarks and the pricier brands listed above, and in my opinion they strike the best balance.

See 10 kinds of chukkas at Thursday’s website.

There are plenty of other brands out there that we deliberately left off (Timberland’s chukkas are ugly, they just are), but what do you think the list is missing?

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Nick English

By day: Manhattan-based journalist with reporting experience on four continents, published in Vice, Men's Health, Popular Science, and a bunch of other places.By night: ravenous consumer of anything and everything related to high end men's boots.Stridewise is where I nurture a maniacal obsession with footwear and share my findings. Say hey: [email protected].

2 thoughts on “The 5 Best Chukka Boots You Can Wear With Shorts”

  1. Hey Nick,

    I’m pretty new to the boot obsession. It’s now January and a lot of boots I’m look for are out of stock. Could be the holiday buying but you would think that the manufacturers would be getting stocks back up now. Then I started thinking that they want the current supplies to run out before the “new model year.” I was wondering, is there a time of the year when they bring out new boots? When would that be and where is it announced?


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