It was a Saturday afternoon in mid-December when I finally embraced it. Staring into a full-length mirror, examining the suit I’d just put on, I put my hands in my pockets—and I couldn’t see the outline of my knuckles. The gravestone would read Here Lies His Slim Pants, 2011–2019, but the death warrant was written a while ago.
It took this moment to have the epiphany, but the truth is that I’d been thinking about moving on to more generously cut trousers for the better part of two years. This was the first time I’d felt good in a pair, but I was standing well on the latter side of their comeback. Fuller silhouettes have been creeping their way back into the zeitgeist over the past half decade. Now, visible kneecaps and the outline of your six-and-a-half-inch iPhone 11 Pro Max are being rapidly traded for clean, straight lines, roomy interiors, and the ability to bend down and pick up your child without literally bursting at the seams.
My aforementioned suit pants weren’t exactly on the cutting edge of the movement, but getting over the hump only put me into a better position to indulge in an aspirational next step: going high-waisted. If finding a little breathing room for your calves was an uphill battle, then pulling your jawns up to your belly button might feel like scaling a rock wall with your hands tied behind your back. Worry not; with the right weapon—like the ones above from Michael Kors—you’ll be comfortably equipped with a look that will make both your grandfather and your cool Parisian friend point their cigarette at you in approval. When the pants go up, your silhouette streamlines, ridding your mind of that little whisper of JNCO that sets in when you first read the word baggy (or, perhaps, wide leg).
Once you’re working with the right trousers, finish off your look by keeping the rest simple. The best way to ease into this type of styling is with a well-fitting, tucked-in T-shirt and a jacket that’s long enough to balance the whole thing out. This isn’t an arena where you want to go wild with pattern mixing, but if the trousers are solid and the tee is minimal, a jacket with some texture can add the just-right amount of attitude.
It’s an advanced move, for sure, but one that spans the decades. Cary Grant did it in the ’40s and Harry Styles did it in his recent Saturday Night Live hosting gig. Hell, even Connery’s Bond hiked ’em up in Dr. No. Yes, it will feel odd at first. Yes, strangers will do a double take. But anyone who wore skinny jeans before 2005 knows that feeling. And they’ll feel it again in the late 2030s, when we’re talking about that comeback, too.
This article appears in the March 2020 issue of Esquire.