With a mere four measurements, Keller can eyeball a listing on eBay and know in a second whether it’ll fit him or not—and, more importantly, whether it’ll fit him the way he wants it to, a hard-earned know-how that ensures his shirts are cropped just right.

Abercrombie & Fitch

Premium Heavyweight Cropped Tee


1991 Loose Straight Jeans

School Yourself

High-waisted pants might feel like a dramatic departure from the jeans you’re using to wearing, but in the middle of the last century, they used to be considered just, well, pants. Not sure how to style ’em? For inspiration, high-rise devotee Kevin Montes poured through old family photos and looked to jazz greats like Eric Dolphy, Miles Davis, and John Coltrane. That journey led him beyond cropped hoodies and high-rise jeans, encouraging far snazzier flourishes, like tucking his knit polos into roomy pleated trousers.

You definitely don’t need a PhD in menswear history to pull off the look, but it’s worth noting that pieces like Ben Chemhoun’s beloved vintage fishing jacket, or even a badass waist-length biker, were initially designed for function first, not just vibes. Motorcycle jackets were cut cropped so that “when you sat on your bike and you had your arms up on the wheel, they didn’t bunch at your waist,” says Bare Knuckles’ Keller. These days, you don’t need a cropped jacket and jeans with a 13-inch rise to ride a Harley, but the golden ratio that defines them will still guarantee your work fits look clean as a whistle on the train to the office.

Kartik Research

Cropped Fringed Cotton and Silk-Blend Jacket

Saint Laurent

Wide-Leg Satin Drawstring Trousers

Find a Tailor

In 2024, there’s no shortage of cropped tees and high-waisted pants at every price point, so getting involved is as simple as a couple of quick clicks. The new-and-improved Abercrombie sells a killer riff on the former, while J.Crew’s viral chinos have become a hallmark of its renaissance. If you’re hunting for “ID?!”-eliciting pants, Montes recommends independent labels like Rota and Casatlantic, both of which have carved out a niche hawking an extensive range of gloriously high-waisted trousers.

Keller probably wouldn’t mind if you perused Bare Knuckles’ next drop, but he’s also quick to tout the power of savvy tailoring. A good tailor can do a lot more than you might think—shorten the length of jeans or the sleeves of an old jacket, modify T-shirts (T-shirts!) to sit right above the waist. Start with a piece of clothing that you don’t get a ton of wear out of and “see what it looks like if you were to chop a few inches off,” he says. The DIY route isn’t a total no-go, but if you take a pair of scissors to an old tee a tailor can finish the bottom hem, which will prevent it from rolling up into true crop-top territory after a spin in the washing machine.

Finding a tailor Montes can trust has been crucial for him, too. “Because of my stature, whenever I wear things right off the rack I feel like a little kid in his dad’s clothes. When something fits you well, it looks like it could be thrifted—or it could be $900.”

Banana Republic

Signature Italian Hopsack Wide-Leg Pants


Reissue 98 LX Slip-On Sneakers

What About Shoes?

Good news here: There’s no hard-and-fast rule among the experts on what shoes work best with your new pants. Montes likes to anchor wide trousers with lug-sole loafers and chunkier boots to balance out the added fabric. But unlike their slimmer counterparts, Keller says, looser pants look killer with pretty much every type of shoe there is; he wears his with loafers and boots, sure, but also dainty slip-ons and retro sneakers. A word to the wise: the same pair of pants might puddle over sneakers but land with little to no break over boots, so home in on the shoes you’ll wear them with and tailor judiciously.

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