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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.
Rubinacci Cotton Genny Trousers
Best Overall High-Waisted Trousers
Rubinacci’s pleated ‘Manny’ trousers are a favorite of Pitti Uomo’s snappiest dressers. It’s no wonder, considering the style’s elegant rise and gurkha buckles on the sides. In incredibly insulating wool-flannel, they’re the best pants to wear come winter.
Todd Snyder Italian Brushed Cotton Gurkha Trousers
Best High-Waisted Chino Trousers
Chinos often lean toward the casual end of the menswear spectrum, but in the hands of Todd Snyder, the style has been a refined twist. These high-waisted trousers, inspired by vintage British military uniforms, for instance, feature a sleek double-pleated front and self-belted waist. They’ll pair nicely with a simple tee and corduroy blazer.
Saint Laurent High-Waisted Gingham-Check Trousers
Best Slim High-Waisted Trousers
In the world of Saint Laurent, slim is always in. Designer Anthony Vacarello is deeply inspired by all things Punk and Mod (two movements that are known for promoting skinny silhouettes), offering collections that take elements from these genres and reworking them in ways that feel fresh and modern. And this tapered pair of gingham-check trousers is proof of this sentiment. It’ll definitely work nicely with a black blazer and Chelsea boots.
Mr P. Tapered Cropped Garment-Dyed Organic Cotton-Twill Trousers
Most Versatile High-Waisted Trouser
Ah, the mighty chino, a style that seldom gets recognition in sartorial circles (see Todd Snyder, too). This is perhaps because it is ubiquitous; most men, regardless of personal tastes, have a pair or two tucked in their wardrobe. But thanks to Mr P., the trusty cotton-twill trousers, often cast in a khaki color, gets a high-waisted update. This one has a more muted color, which means it will compliment any top you pair with it. That, my friends, is called versatility.
King & Tuckfield
Best High-Waisted Trousers for Summer
Do you have plans on sipping on Limoncello at a seaside joint on the Amalfi Coast? Is lounging in a cabana in Cuba on the itinerary? The best trousers to pack for any tony sun-filled excursion in the high-waisted from King & Tuckfield. Made of 100 percent cotton in a cream color, these pants are breathable, durable and fully imbue the sweet life.
Officine Générale Luigi Pleated Wool Pants
Best High-Waisted Trousers for the Weekend
Made of pleasted wool, Officine Générale’s trousers look incredibly spiffy. The pleats and slightly dropped crotch makes this pair particularly comfortable. Team with a knit polo and sneakers for a polished off-duty look.
J.Crew Kenmare Pleated Suit Trousers
Best High-Waisted Trousers for the Office
Though dressing up for the office may not collectively rank as high as did in the past, there are still some professions that enforce a formal dress code. And if you happen to have one of these gigs, J.Crew’s high-waisted trousers in foolproof navy blue will more than suffice. Wear it with a streamlined button-down, tie and oxfords, and consider yourself primed to conquer the corporate world.
Amiri Wool Flare Cargo Pants
Best High-Waisted Cargo Pants
We can always expect a high level of cool from Mike Amiri. Season after season, the designer never fails to bring his signature streetwise edge to fashion stalwarts. And a prime example of this sentiment are these high-waisted wool cargo pants.
Celine Homme Cropped Wide-Leg Pleated Wool-Gabardine Trousers
Best Cropped High-Waisted Trousers
If you want to enjoy high-waisted pants but with a more renegade attitude, this skater-inspired pair combines a traditionally roomy seat with a cropped length. We suggest leaning into the casual side of things with a turtleneck or a tee come summer.
Suitsupply Grey Vigo Trousers
Sharpest High-Waisted Trousers
When it comes to razor-sharp suits, Suitsupply is the name to know. The brand offers a full range of styles, from linen pants to camel blazers, all which feature incredibly streamlined silhouettes. Of course, its high-waisted pants fit the same bill, this one made of gray cotton stretch that’ll gel nicely with a ribbed sweater or shawl collar cardigan.
Studio Nicholson Bill Cotton-Twill Chino Trousers
Best Casual High-Waisted Trousers
High-waisted needn’t mean dressy, as evidenced by this pair of everyday chinos. As such, they offer the elegance of a high-waisted silhouette for even the most unremarkable coffee runs or weekend strolls. Dressed up with an unstructured jacket or casually with a sweatshirt, these prove how easy high-waisted trousers are to wear.
Comme Des Garçons Homme Cropped Straight-Leg Pants
Best Unique High-Waisted Trousers
Always expect Comme Des Garçons to deliver silhouettes that color outside the lines. The storied brand is celebrated for its avant-garde collections filled with looks that push the boundaries of design. That said, it also offers pieces, like this high-waisted trousers, that are completely wearable. The silhouette may be wider and stouter than standard pants, but for true fashion lovers, this is what makes styles from CDG a cut above the rest.
Merely Made Wide-Leg Pleated Cotton-Drill Trousers
Best Wide-Leg High-Waisted Trousers
A pair of high-waisted trousers is already uncommon (regrettably), but factor in wide legs, and many might keep scrolling. Don’t follow the status quo. Be the sartorial leader that you know you are and try out these pants from Merely Made. Yes, they are high-waisted. Yes, they feature a wide leg. But when paired with a simple tee or a great shacket, you’ll have a look that’ll put you on top of the style podium.
Albus Lumen Pleated Merino Wide-Leg Trousers
Best High-Waisted Wool Trousers
Albus Lumen is another brand that offers wide-legged, high-waisted trousers, this one made of merino wool. This means it is much more refined, a style better suited for a sharp button-down and spiffy pair of loafers.
Casatlantic Tanger Trousers
Best Retro-Inspired High-Waisted Trousers
High-waisted pants aren’t new for Nathaniel Asseraf. “I only ever wear them,” he says. A tasteful update of styles from the 1950s, Casatlantic’s trousers are versatile and thoughtfully-crafted (even down to the zipper length). As Asseraf will tell you himself, “I’ve designed my collection to never go out of style.”