3 ways to style Bermuda shorts for colder days

You might think I’m crazy to tell you that we’re now entering shorts season. But… we are entering the best part of shorts season! I can explain. Autumn is the season rentrée– you know, the elegant French way of saying “back.” Our schedule is full of responsibilities, some fun, some less. It’s time to get dressed and the weather is only changing gradually. So while our favorite wool pants may be tempting us, it’s entirely possible that temperatures may not yet be so in tune with our cozy fall aspirations. Enter short Bermuda shorts. Specifically, these suit-like wool shorts, which are simply a shorter version of your favorite trousers. They’re wardrobe heroes this time of year because they’re so easy to style with everything else we can’t wait any longer to wear: sweaters! Loafers! Leather jackets!

Designers agree. The Row showed a wool and silk suit with Bermuda shorts and knee-high leather boots for fall 2024. Chanel showed a pink tweed version. Prada showed knee-length silk habatai briefs paired with a back-to-school leather bomber jacket. Chemena Kamali continues the idea of ​​winter shorts for the holidays, presenting the Chloé Resort 2025 show full of shorts styled with leather jackets, knee-high boots and flowing evening tops.

The beauty of Bermuda this time of year is its chameleon-like quality. Often we may want to wear a skirt or dress, but we hesitate because we are unsure about what to wear. Shorts can be interpreted as elegant or casual, easily fitting into a group look among a sea of ​​jeans or cocktail dresses. Due to their length, they are also breathable, which is perfect for cable-knit shoes and closed-toe shoes. They let you get dressed without feeling like you’ll be underdressed by 2 p.m. Below are three ways to style Bermuda shorts for fall days and nights.

Photo: Courtesy of Becky Malinsky

Daily grind

Leaving the house in the morning feeling fully styled and not just in jeans and a sweater means ditching the jeans. Wool trousers or silk trousers, cotton skirt or brocade skirt. Everything but jeans and a sweater comes at 9:00 if I want to feel like I have even the slightest advantage on that day. Considering we’re just starting to see the leaves change and the temperatures drop in New York, I’m not ready to spend much time there yet. Cropped Bermuda shorts with a wool gray suit make me look completely immersed in the season while revealing the slightest hint of a tan that lasts well into October. I’m wearing my favorite fall pair from Brunello Cucinelli, an old Prada knit, a white T-shirt and my new viral Bally loafers. Last week, I took my laptop with me to two meetings and orientation at my son’s school in this outfit, and by 4 p.m., I felt just as comfortable. like when I left the house this morning.

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Photo: Courtesy of Becky Malinsky

Suit relief

At 175 cm tall and a size 4, I don’t feel statuesque enough to wear a completely oversized suit with a jacket, baggy trousers, a turtleneck and flats. While I love the minimalist 90s look in theory, the sheer amount of material blew me away. With blazer season upon us, Bermuda shorts have become a welcome addition to the rotation – the extra leather happily balances out the very structured and fully covered turtleneck and blazer. I’m wearing sharp shorts from Róhe Frames and my vintage +J Uniqlo two-button blazer, but any navy blue style will do. Cos merino turtleneck, my shoes are Tory Burch and my bag is The Row.

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Photo: Courtesy of Becky Malinsky

Dress code: J.Crew

Last month, just seconds after Labor Day, I was invited to an “intimate” J.Crew Fashion Week dinner for 500 guests at the New York Public Library. Given its scale, you’d think I knew someone well enough to text and ask what they were planning on wearing. However, when I asked my friends if they planned to come, I still did not meet my expectations. Panic set in and I began to feel incredibly insecure about what I was wearing – it was technically a cocktail party, but hosted by the kings and queens of prep and without the safety net of a group of work friends by my side. I wanted to feel appropriate and special, but, God forbid, overdressed. After trying on countless combinations with my bed piled high with clothes, I settled on a navy wool pair from the brand (one size up for a good slouch!) and wore a button-down shirt, tucked in, and some party heels. The shorts made me feel like I was chic enough among the tuxedos and slips, but not so dressed up that I wouldn’t fit in if everyone showed up in what they had been wearing all day. It ended up being… perfect.

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