That’s 15 Best High-Waist Pants and How to Wear Them

If you purchase an independently reviewed product or service through a link on our website, Robb Report may receive an affiliate commission.

Once upon a time, high-waisted pants were the norm in men’s fashion. Then, about two decades ago, certain false prophets came to tell us how they belonged to Grandpa’s sepia photos (or 1930s Chicago smugglers) and that we were better off with thin, or worse, thin, low-rise silhouettes if we wanted to stick with the program. But that’s about to change.

With wider cuts dominating the runway, as well as the revival of James Dean style T-shirts, the high-waisted pants are back. As Porter’s director of style, Olie Arnold, tells us: “For a few seasons now, we’ve witnessed the evolution of leaner tailoring towards a more relaxed and functional offering.”

Comfort is a key factor in the way men shop and dress today, “especially given the non-traditional office environment,” Arnold said, “there’s a taste for lethargic, flowing silhouettes.” Even if the baggy pants on the runway are too extreme for your taste, there are plenty of pieces inspired by 1930s Hollywood, espresso-consuming Neapolitans, and military surpluses. It’s not a trend like a return to shape.

Nathaniel Asseraf, the man behind the Swedish vintage emporium Broadway & Sons, created modern pants informed by his vintage experience. With  his Casatlantique  brand, Asseraf says, “My mission is to make pants that look good for anyone and the high-waisted, wide-legged pants match most body shapes, and even add height.” Always good news for the shortest among us.

For Asseraf, there are a few things to consider before buying: “You can use it with anything, as long as the proportions are appropriate. What you wear on your body has to be shorter in length or it will create an imbalance.” He also offered advice for those who want to extend: “Remember to modify them to rub against the top of the shoe, or they will have the opposite effect.” As for size, rather than measuring the waist around your hip bones, as you would with low pants, she suggests taking measurements around your navel. Depending on your perseverance with the stomach, this can mean assessing its size.

Arnold suggests keeping the combination simple, such as a tucked T-shirt or a knitted polo shirt. His pro suggestion? Go without a belt. “It puts the focus on sewing without dividing the silhouettes. The pants are pièce de résistance here, so comfort with a marked style. And if you want to wear it in more formal moments, wear a well-made jacket or blazer for more structure.”


Leave a Reply

Your email address will not be published. Required fields are marked *