The Bermuda Shorts Trend Is the Unexpected Winter Style You Didn’t See Coming

Whispers are swirling amongst the fashion crowd that the Bermuda shorts trend is making an unconventional comeback this season. While initially I wasn’t sure this quintessential summer style would find its way into my cold-weather wardrobe, Katie Holmes has convinced me otherwise.

She recently wore blue Bermuda shorts that hit right above the knee while roaming around in 30-degree weather. Although it seems quite risky to style thigh-grazing shorts for frigid temperatures, she did so in a way that makes sense. The actress teamed her winter outfit with a snug double-breasted coat, a cozy knit hat, and an oversized button-down shirt. She covered her legs with sheer black tights and slipped into matching loafers. Meanwhile, Kiera Knightly styled the unexpected winter-proof Bermuda shorts trend with sleek knee-high burgundy boots.

According to Trendalytics Director of Trend and Editorial Strategy Kendall Becker, Holmes 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. Even style icons like Charli XCX and Rihanna have winterized this breezy style with cowhide boots and faux fur coats.

Outside of celebrity circles, fashion fans are also catching onto the craze. “The Bermuda shorts trend is resonating well amongst consumers," says Becker, who notes that the rise in popularity of Bermuda shorts is also reflected in the fashion options on the market. Becker explains that, on average, retailers have increased their Bermuda shorts offerings by 87 percent compared 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.”

With that in mind, we've curated 10 Bermuda shorts outfits that boast winter-friendly appeal—even for the skeptics out there. “They look just as good styled with a tank top as they do with a chunky sweater," says Becker. So, go ahead and try them for yourself.

Rodeo-Ready

Try two trends at once by styling a pair of Bermuda shorts with 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 winter. Complete the look with a wool-blend coat that adds an undeniably polished touch.

A Splash of Color

“Instead of styling a pair of Bermuda shorts with a sleek tank as you would for summer, opt for layers,” says Maguire. Consider a burgundy blazer that falls in line with the latest color trends. And if you’re in the mood to stand out even more, play into the loafers-and-socks styling hack.

On the Clock

For those winter days that feel like fall, throw on a tailored blazer and a coordinating pair of Bermuda shorts. With their mid-length inseam and roomy fit, you can easily wear them to work without worrying about breaking dress code rules.

Against the Grain

Who says white pants (or cream in this scenario) must be reserved for summer? Feel free to break the outdated no-white-after-Labor-Day rule by incorporating this look into your winter outfit rotation. Anchor the look with platform heels, and if you get a bit chilly, throw a jacket over your shoulders.

Outfit Repeater

The blazer-and-Bermuda-shorts combo is one that is absolutely foolproof. Once you discover how little effort this outfit formula takes to achieve, you’ll be wearing it on repeat.

All Bundled Up

“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 winter 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 t-shirt to a sweater. Then, pile on a fur coat or a parka for extra warmth.

Proportion Play

“While my mind immediately goes to styling Bermuda shorts with a kitten heel, I also plan to try them with boots,” 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 trick, and you’ll look incredibly cool,” she adds.

Out on the Town

Winter might be upon us, but that doesn’t mean we’re staying inside. Try on a pair of Bermuda shorts and a wrap coat for a classy night out. Maguire mentions that you can also add an extra layer to your bottom half. “I love styling my Bermuda shorts with hosiery—it’s a great way to bring your fit from day to night,” she adds. Finish off the look with pumps and a hardware-adorned handbag.

Back to Basics

There's no need to overthink a Bermuda shorts outfit. Sometimes, the best looks keep things simple from head to toe. Take notes from this fashion week showgoer and reach for a cozy cardigan, a trench coat, and a pair of simple black boots.

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.