As promised in my earlier Fall and Winter Boots: My Favorite Styles post, I'm rolling out a guide for each of the featured boots with background information and examples of how to wear them.
Kicking off this series is the most comfortable boot on the block – the Chukka.
All Desert Boots are Chukkas, but not all Chukkas are Desert Boots. Confused? Good, let me explain.
The terms Chukka and Desert boot are sometimes used interchangeably, but there are a few differences.
To briefly explain, a chukka is a two or three eyelet ankle boot that’s made of two pieces of leather (a front piece and a back piece), has a plain toe, and a leather sole.
Desert boots are a type of chukka and share the same ankle height and number of eyelets, but have a natural crepe rubber sole and are more casual in both materials and construction.
Chukkas can be found in a broad spectrum ranging from quite formal to extremely casual.
On the left, you can see an example from Ralph Lauren (similar). Note the smooth leather, sleek profile, pointed toe, and leather sole.
This makes for a boot that can be worn to the office during the day, out to dinner in the evening, and casually on the weekend.
On the right is the famous Clarks desert boot. Note the suede uppers, flat laces, rubber sole, unfinished edges, and wider profile.
All these characteristics make for a shoe that is best paired with casual attire.
There are many theories about the actually origin of this boot style but for simplicity, let's just say that the desert boot style was adopted by British soldiers in the Western Desert Campaign of WWII.
Nathan Clark, of Clarks Shoes, first noticed this style on a trip to Burma. He introduced the Desert Boot to America at the 1950 Chicago Shoe Fair.
They then became popular with beatnik generation and mod movement of the 1950s and 60s.
These are the most comfortable shoes I've ever worn!
Seriously, they’re the only shoe that doesn’t force my foot to conform to some cruel and unnatural shape.
Desert Boots are so comfortable, in fact, that the first time I laced them up, I expected to take a step and walk right out of them.
To my surprise, they stick to your feet like glue, moving with you perfectly. It actually took quite a while to get used to their lack of interference.
This boot is comfortable in the way that your house slippers are comfortable – no ankle support, motion control, steel shank, or arch support here. Just good looks and pure comfort.
How to Wear
Desert Boots are your new sneakers. Really, leave the Nikes in your gym bag. These are just as comfortable, lace up without fuss, and look great with any casual outfit.
Desert boots look great with jeans, casual trousers, and I’ve even seen some fashion forward people wear them with shorts (experts only). Below are a couple of potential looks that pair nicely with desert boots.
Cotton Trousers and a Fitted Button Up
Raw Denim and an Oxford Cloth Button Down
When shopping for chukkas, you'll encounter a wide range of prices depending on type and construction of the boot.
One hint though: if you're opting for a desert boot, there's no reason to look elsewhere beyond Clarks.
That said, here are some great options from cheapest to most expensive:
Mid – Cole Haan Cambridge
So how do you like to rock your chukkas? Dressed up or down? Let me know in the comments below!