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 for this use case — it’s already a dicey proposition to wear chukkas with shorts, so you have to make sure you get it right. So for this short list, 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 — OK, one reason is that it’s inexpensive. But it’s also about as close to a sneaker as a boot gets: the sole is super soft and ideal for guys that prefer lightweight, breathable footwear in hot weather.

With floppy suede and a crepe sole, this is an unambiguously casual chukka, which is another reason people are comfortable wearing them with shorts. You absolutely don’t want to wear a nice calfskin chukka with dressy leather soles when you’re looking for one to wear with shorts.

The crepe sole won’t last long, the lack of shank means some guys find them too squishy to wear all day, and cobblers tell me there’s about a 50/50 chance of these boots surviving a resole, but if you’re looking for soft and casual.

2. Red Wing Heritage Weekender Chukka

It can be hard to figure out which boots are casual and super high quality, but Red Wing Heritage has really figured out their Weekender Chukka.

This all USA-made brand is better known for their super tough, Goodyear welted boots, but the Weekender line (which includes a similar Chelsea) is made differently: lightweight crepe soles, stitchdown construction, and seriously high quality leather uppers means these chukkas are far longer lasting than they might appear.

Red Wing also has the heavier Work Chukka (above) which is made with work boot leather and a Goodyear welt, and honestly, you could wear those with shorts too: the most important element of shorts-suitable chukkas is casual, and the Work Chukka has the roomy toe, shiny eyelets, and a wedge sole that put it more firmly in the work category than almost any other chukka.

But for breezy summer shorts wear, people tend to like chukkas that are light and airy themselves, and that’s the Weekender Chukka for sure.

3. Jim Green’s Vellie

For a chukka that reads tough, outdoorsy, and ready for a hike, Jim Green’s Vellie deserves your attention.

This small South African brand has a lot going for it: their boots are resoleable, outdoorsy, roomy, every purchase contributes to free boots they donate to theGame Rangers Association of Africa, and there’s a case to be made that the desert boot was invented in South Africa.

So these ones stand out for their roomy fit that makes it easier to do outdoor activities and easier to wear them with shorts, they have different leathers and soles to suit your preference, and they’re really inexpensive — $150 for chukkas that are way more durable than Clarks.

4. Astorflex’s Brownflex

This is a great option for guys who want a chukka that’s more on the premium side, but still 100 percent appropriate for casual wear.

Astorflex is made in a small workshop outside of the Italian city of Milan and they’re really focused on suede uppers and crepe soles — it’s how they make their Chelseas and a lot of their loafers, but among guys in the know, suede upper and crepe sole brings just one kind of footwear to mind: the chukka.

More specifically, the desert boot, which is what you call a chukka with a suede upper and a crepe sole, and you should know that it’s the only kind of chukka these guys make.

Fortunately, that’s the kind of chukka you should wear with shorts, especially when it’s got this kind of roomy toe and flat cotton laces. Made in Italy, resoleable, and $250, this should scratch the itch of guys wanting something elevated they can dress down.

5. Thursday Boot Company’s Scout (with the wedge sole)

Thursday has made an indelible mark on American footwear by bringing resoleable boots to the masses: by making their bestselling boots with comfy foam insoles and selling them at under $200, they’ve converted scores of guys to high quality footwear.

Their brand is also known for boots that are smarter than work boots but more casual than dress boots, and it’s true that their Scout is more on the tapered, almond-shaped toe side than others on this list.

But that’s why you should opt for their Rugged and Resilient Scout boots. They’re made with work boot leather uppers and casual wedge soles, putting them firmly in the “casual” camp and making for a delightful balance of smart and tough that can work well with shorts.

There are plenty of other brands out there that I deliberately left off (Timberland’s chukkas are ugly, they just are), but I think that’s a solid mix of different kinds of chukkas that can dress way down.

The key to wearing chukkas with shorts — even if you’re trying for something closer to smart casual — is to look for a round toe and a soft sole. Would you add any other model to this list?