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The 15 Best High-Waisted Pants—and How to Wear Them

It's not a trend so much as a return to form.

best high waisted trousers

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Once upon a time, high-waisted trousers were the norm in menswear. Then, about two decades ago, certain false prophets arrived to tell us how they belonged in sepia photos of grandpa (or 1930s’ Chicago bootleggers) and that we were better off with slim—or worse, skinny—low-rise silhouettes if we wanted to get with the program. But that’s about to change.

With roomier cuts dominating the catwalk, as well as the revival of the tucked-in T-shirt à la James Dean, high-waisted pants are back. As Mr Porter’s style director Olie Arnold tells us: “For a few seasons now, we’ve been witnessing the evolution from slimmer tailoring toward a more relaxed and functional offering.”

Comfort being a key factor in how men shop and dress today, “especially in light of non-traditional office settings,” Arnold says, “there’s an appetite for a languid, fluid silhouette.” Even if the wide-legged trousers on the runway are too extreme for your taste, there are plenty of pieces inspired by 1930s Hollywood, espresso-guzzling Neapolitans and military surplus. It’s not so much a trend as a return to form.

Nathaniel Asseraf, the man behind Swedish vintage emporium Broadway & Sons, is creating modern trousers informed by his vintage expertise. With his brand Casatlantic, Asseraf says, “My mission was to make pants that would look great on anyone and high-waisted, wide-legged trousers suit most body shapes, and even add height.” Always good news for the shorter-in-stature among us.

For Asseraf, there are a few things to consider before buying: “You can wear them with anything, as long as proportions follow. What you wear on your torso must be shorter in length or it will create imbalance.” He also offers a word of advice for those looking to lengthen: “Remember to have them altered to skim the top of the shoe, or they’ll have the opposite effect.” As for sizing, rather than measuring the waist around your hip-bone, as you would for low-rise trousers, he suggests you take the measurements from around your belly-button. Depending on your diligence with crunches, this might mean sizing up.

Arnold suggests keeping your pairings simple, like a tuck-in tee or knitted polo. His pro tip? Go beltless. “This puts the focus on the tailoring without splitting the silhouette. The trousers are the pièce de résistance here, so take comfort in the dialed-down styling. And if you want to wear them in more formal moments, throw on a well-tailored jacket or blazer for more structure.”

Here are 15 of the best options to buy now.

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