Bermuda Shorts Outfits to Style for Early Fall

Earlier this year, There were whispers amongst the fashion crowd that Bermuda shorts were poised to make a grand comeback in 2024. While I wasn’t convinced that this quintessential ‘90s style would find its way into fashion’s contemporary trend cycle, that all changed a few months later when I stumbled upon an Instagram post by Ayo Edebiri.

The actress posed in a custom iteration of Bottega Veneta’s turquoise suit set from the label’s Pre-Fall 2024 collection. The look was styled with a silky button-down top, a blazer anchored in slightly oversized shoulder pads, and a pair of Bermuda shorts that hit right below the knee and were tailored to perfection. Edebiri’s Bermuda shorts look unequivocally stole the show and created a buzz across fashion news outlets, proving the style can compete with the best of 2024's trending popular summer styles, from bubble skirts to mesh flats to capri pants.

According to Trendalytics Director of Trend and Editorial Strategy Kendall Becker, Edebiri is just one of many A-listers taking the Bermuda short for a spin. “Bermuda shorts have become a street-style favorite among stars like Hailey Bieber, Irina Shayk, and Suki Waterhouse,” she notes—and outside of celebrity circles, fashion fans are also catching onto the craze. “The Bermuda shorts trend is resonating well amongst consumers—the social buzz is up 17 percent in the last 90 days," says Becker.

The rise in popularity of Bermuda shorts is also reflected in the fashion market options. Becker notes that, on average, retailers have increased their Bermuda shorts offerings by 87 percent in comparison to last year.

“We’ve had Bermuda shorts on our site for a while now, but we’re adding more to the mix as we stay on top of trends and anticipate what our customers want,” says Shopbop Senior Fashion Director Caroline Maguire. These include tailored options by brands like Favorite Daughter, Vince, and Róhe and denim styles from Coperni, Good American, and DL1961. “I’m currently loving Agolde’s ‘90s Shorts and Posse’s Wesley Shorts,” adds Maguire.”They’ve become staple pieces in my wardrobe.”

It’s clear that Bermuda shorts have quickly become a warm-weather favorite, and we anticipate this style transition will continue to gain headway through the fall. “Bermuda shorts are the perfect versatile option for in-between season dressing, especially because of their longer inseams,” Becker explains. “They look just as good styled with a tank top as they do with a chunky sweater."

With that in mind, we've curated 10 Bermuda shorts outfits that flaunt a fall-friendly appeal—even for the skeptics out there. Don’t say we didn’t warn you.

Rodeo-Ready

Try two trends at once by styling a pair of black Bermuda shorts with matching cowboy boots that practically scream, "Take me to the rodeo." And yes, the Western trend is still going strong as we make our way into fall. Offset the look with a crisp white button-down shirt that adds a polished touch appropriate for work.

A Splash of Color

“Instead of styling a pair of lightweight Bermuda shorts with a sleek tank as you would for summer, opt for a transitional knit sweater,” says Maguire. The style expert recommends adding an embellished belt and a pair of strappy sandals to make a statement. And if you’re in the mood to stand out, accessorize with a pop of color, like an emerald-toned bag—shades of green are going viral this fall.

On the Clock

For those fall days that feel like summer, throw on a tailored vest and a coordinating pair of Bermuda shorts to beat the heat. With their mid-length inseam and roomy fit, you can easily wear them to work without worrying about breaking dress code rules. “Complete your office outfit with kitten heels to take your look from your desk to the dinner table,” says Becker.

Against the Grain

Who says all-white outfits (or all-cream in this scenario) have to be reserved for summer? Feel free to break the outdated no-white-after-Labor-Day rule by incorporating this look into your fall outfit rotation. Anchor the look with black accessories and a pair of pointy flats, and if you get a bit chilly, throw an oversized cardigan over your shoulders.

Outfit Repeater

It appears as though Ayo Edebiri isn’t the only one pairing power blazers with Bermuda shorts. The look can also be dressed down for every day by pairing tailored separates with a plain black T-shirt. Once you discover how little effort this outfit formula takes to achieve. you’ll be wearing it on repeat.

Denim on Denim

“As the weather starts to get colder, consider styling your Bermuda shorts with a basic tee layered beneath an oversized jacket,” says Becker. A leather jacket or a barn jacket will certainly do the trick. Or opt for a denim jacket and give your look a Canadian tuxedo twist with a pair of jorts (a.k.a the denim version of Bermuda shorts). If you need more convincing, note that celebrities like Beyoncé, Bella Hadid, and Jennifer Lopez have all co-signed the double denim trend.

Layer It On

“The key to styling Bermuda shorts for fall is to add several layers to your look,” says Maguire. You can achieve that with an oversized blazer that can fit over any type of top, from a peekaboo tank to a chunky sweater. Maguire mentions that you can also add an extra layer to your bottom half. “I love styling my Bermuda shorts with hosiery—it adds a hint of warmth, and it’s a great way to bring your fit from day to night,” she adds. Finish off the look with power pumps and a hardware-adorned handbag.

Proportion Play

“While my mind immediately goes to styling Bermuda shorts with a kitten heel, I also plan to try them with boots this fall,” says Becker. But not just any boots—Becker shares that Bermuda shorts look best with knee-high boots that will instantly balance the proportions of your outfit. “Use this styling hack, and you’ll look incredibly cool,” she adds. If the weather permits, try pairing your look with a buttoned vest.

Out on the Town

While fall is around the corner, we’re still bound to have a few more balmy evenings to take advantage of. Slip into Bermuda shorts, a lace-trimmed corset top, a shimmery gold handbag, and sleek heels for an end-of-summer night out.

Back to Basics

There's no need to overthink a Bermuda shorts outfit. Sometimes, the best looks keep things simple from head to toe. Choose a sleeveless mock neck top (or a long-sleeved turtleneck if the weather demands extra coverage) and pull on a pair of pleated Bermuda shorts. Reach for ballet flats that play into the girlhood aesthetic trend for a bit of girlish charm.

Meet the Experts

Kendall Becker

Experienced in luxury editorial, trend forecasting, and strategic consulting, Becker is currently the director of trend and editorial strategy at Trendalytics as well as a freelance writer. Prior, she was the assistant fashion director for women's RTW at Bloomingdale’s and contributed to global trend forecasting agencies. Becker is also a fashion media personality and expert.

Caroline Maguire

As Shopbop Senior Fashion Director, Caroline Maguire brings her signature style, keen eye, and over 20 years of industry experience to the role. Since joining the organization in April 2016, Caroline has partnered closely with creative, buying, PR, and marketing team members to determine fashion direction across the company. She also serves as Shopbop’s primary brand ambassador in press interviews and media appearances, and delivers key style takeaways to the customer in creative onsite editorials.