I'll Give Up Desert Boots When You Pry Them Off My Feet

The trend cycle moves at a breakneck pace; the second you decide to hop onboard, the ship has already sailed. While clothes seem to have more of a never ending deluge of trend shifts, shoes can also be hard to keep up with. In the footwear space, there are a few options that come to mind that are trend-proof and never kowtow to what’s “in”: the Clarks Desert Boots happen to be one of those shoes.

The Desert Boot was officially launched in 1950 by Nathan Clark, the great-grandson of the company’s founder, after he noticed officers in Burma wearing rough suede boots with crepe rubber soles. Seventy-six years later, one of the defining features of the Clarks Desert Boot is its bouncy rubber crepe sole. It differs from other chukkas, which can use leather soles or other sturdy rubber outsoles. Desert boots are also unlined and super flexible, a detail that adds to its endearing casualness.

As someone who prides himself on not jumping on trends, I figured that with fall finally in the air, and fresh foliage on the ground, now’s a good time to revisit this footwear stalwart. They are still one of the best boots thanks to their malleable nature; they can be worn with a variety of jackets or different washes of jeans, chinos, and work shirts. Below is a breakdown of how I styled my pair three different ways.

Outfit 1: The Autumnal Go-To

If Mother Nature didn’t exist, I’d dress like this year-round. The cola suede colorway on the Desert Boots makes them an easy neutral to pair with just about anything in your fall wardrobe. Ecru is one of my favorite shades to wear, as it always pairs well with brown hues, and my Jungmaven tee has that washed-down, vintage T-shirt feel that drapes perfectly.

For denim, these 1947 LVC 501s have been getting a lot of wear lately. I actually think they did a great job with the pre-darning and mending on these jeans, which gives them a hint of character without looking like a homemade distressing attempt.

This has easily been one of my go-to outfits for making the transition between seasons a little easier. The mornings start brisk, temperatures jump up around noon, and suddenly you’re trying to figure out which season it is, which is why a good piece of knitwear on standby is never a bad option.

Outfit 2: Denim Dad

A denim shirt and chinos are about as safe as an outfit can get, but you’ll never regret wearing some version of this, or at least that’s what I keep telling myself. Ever since becoming a dad five years ago, my denim-shirt collection has multiplied tenfold. They’re versatile, easy to wash, and somehow look better the more stains and rips they collect—and built for parenthood.

I’m wearing mine with some baggy chinos from Gap, which, I must say, might take the crown from the J.Crew Giant Chino in my humble opinion. I’ve been wearing this combination while working from home, running errands, and walking to pick my son up from school. It’s comfortable, but still gives the illusion of effort.

Outfit 3: City Safari

Maybe it’s the Midwesterner in me, but there’s something so liberating about wearing a long-sleeved shirt, jacket, and shorts this time of year. I once saw an artist featured in Mr Porter’s The Way I Dress video series from back in the day who went sockless with his Desert Boots, and I understand it now. That’s the beauty of the unstructured upper and the comfort of the crepe rubber sole: they make going sockless feel a little less questionable.

The shorts from Filson have a decent amount of volume, but they don’t feel too baggy. Maybe I’ve been looking at too many old Banana Republic catalogs, but there’s something about this combination that feels interesting. All I need now is a Land Cruiser and an expensive pair of binoculars.