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.
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.
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.
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.
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.
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.
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?