Kendall Jenner’s Stylist Shares Her Tips For Wearing Bermuda Shorts

Some trends ascend at warp speed but end up fizzling out of the fashion scene just as fast. You know the ones — by the time you finally decide to give ‘em a go, they’re no longer relevant. That’s not the case with Bermuda shorts, though. Returning to the spotlight around 2019, the knee-skimming bottoms have only gathered speed over the past few years. Perhaps that’s because, unlike its hip younger sister, cheeky cutoffs, Bermudas are suitable for almost every occasion, from the office (well, depending on your job) to laid-back weekend get-togethers.

Dani Michelle, a celebrity stylist who dresses It girls like Kendall Jenner and Hailey Bieber, points to the shorts as the ultimate transitional piece. Her best advice for wearing them? “I love mixing proportions, so if you have a looser bottom, I like a smaller fitted top,” the expert, who was recently named the creative director of Joe’s Jeans, tells TZR.

Similarly, Chloé Harrouche, a content creator and the founder of Loulou de Saison, suggests playing with contrasts. “Either elevate the shorts with a sharp blazer and statement heels like the SIAM, or lean into casual and ease with a pair of leather flip-flops to soften the silhouette,” she says. Another draw is the variety of options out there. “Bermuda shorts work for different seasons in different fabrics like denim and suiting materials [for the spring] and linen in the summer,” notes Favorite Daughter’s creative director, Carla Calvelo.

Below, find more Bermuda shorts styling outfit ideas for spring and beyond.

A Perfect Balance

When it’s not quite warm enough to slip into a pair of strappy sandals, pair your Bermuda shorts with a knee-high boot, revealing just a sliver of skin. Rihanna and Bella Hadid are fans of the combo, should you need further convincing to take it for a spin. From there, take Michelle’s advice and offset baggy bottoms with a form-fitting jacket.

Leather On Leather

Two leather pieces are better than one, yes? Harrouche certainly thinks so, as she teamed her knee-length shorts in the material with an oversized jacket. The leather-on-leather look also works with a jacket if you’re one to run cold.

Office Apt

Bookmark this formula for a summer work outfit that won’t get you flagged by HR. A crisp white button-up alongside tailored Bermudas is undeniably chic — especially if you add a polished heel to the mix.

Poolside Cool

No need to wait to map out your upcoming poolside looks. In some parts of the country, you may be able to lounge near the water in the coming weeks. And when you do, wearing your bikini top with denim Bermudas short is a smart move. After all, a chill afternoon is better with a refreshing iced coffee from your local spot.

Night Out

With a sumptuous cape-style top and flirty ballet flats, neutral Bermuda shorts can seamlessly transition into the evening, whether you’re grabbing drinks with a friend or going on a first date. Tote around a suede bag for an extra dose of polish.