3 Ways to Style Bermuda Shorts for Cooler Weather | Vogue

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You may think I’m insane for telling you we are just entering shorts season. But…we are entering the best part of shorts season! I can explain. Fall is the season of rentrée—you know, the chic, French way of saying reentry. Our schedules are chalk full of obligations, some fun, some not so much. It’s time to get dressed and the weather is only gradually turning. So while our favorite wool trousers might be beckoning us, it’s quite possible that temperatures might not be quite as aligned with our cozy autumnal aspirations just quite yet. Enter the Bermuda short. Specifically the wooly, suit-like short that is basically just a shorter version of your favorite slacks. They are a wardrobe hero this time of year due to their styling ease with everything else we can’t wait a moment longer to wear: Sweaters! Loafers! Leather jackets!

Designers agree. The Row showed a Bermuda bottomed wool and silk suit with leather knee-high boots for fall 2024. Chanel followed with a pink tweed iteration. Prada showed silk habatai knee-length bloomers toughened up with a very back-to-school leather bomber jacket. Chemena Kamali continues the shorts-for-winter idea into holiday, packing the Chloé resort 2025 show full of shorts styled back to leather jackets, knee-high boots and flouncy evening tops.

The beauty of Bermuda shorts this time of year is their chameleon-like quality. We may often want to wear a skirt or dress but hesitate, unsure of the dress code. Shorts can be interpreted as dressy or casual, easily integrating into a group setting among a sea of jeans or cocktail dresses. They’re also, by nature of their length, breathable for when you’re ready for a cable knit and closed-toe shoes. They let you layer up without feeling like you’ll be dressed all wrong by 2 PM. Below, three ways to style Bermuda shorts for fall days and fall nights.

To get out the door in the morning, feeling fully styled and not just like I threw on jeans and a sweater, is to ditch the jeans. A wool pant, or silk pant, or cotton skirt or brocade skirt. Anything but jeans and a sweater come 9 AM if I want to feel like I have at least the slightest edge on the day. Given that we are just starting to see the leaves change and the temperatures dip in New York City, I’m not quite ready to go fully long. The Bermuda short in a wooly grey suiting makes me look fully immersed in the season while showing off the slightest hint of a tan enduring into October. I’m wearing my favorite fall pair by Brunello Cucinelli here with an old Prada knit, a white T-shirt, and Bally’s new viral loafer. I shlepped my laptop with me to two meetings and an orientation at my son’s school in this outfit last week, and felt just as good at 4 PM. as I did leaving the house that morning.

Leset

Kelly cropped ribbed jersey T-Shirt

NET-A-PORTER

SSENSE

Uniqlo

merino cardigan

UNIQLO

Brunello Cucinelli

Tropical Luxury wool City bermuda shorts

SAKS FIFTH AVENUE

Bally

Pathy leather loafers

NET-A-PORTER

Róhe

tailored wide-leg shorts

RÓHE

NET-A-PORTER

FWRD

SSENSE

The Frankie Shop

Wilma pleated bermuda shorts

THE FRANKIE SHOP

At 5’5” and a size 4, I don’t feel quite statuesque enough to pull off a fully oversized suit with a blazer, baggy pants, turtleneck, and flat shoes. While I love the minimal ’90s look in theory, the sheer amount of fabric would swallow me. So as blazer season roars in, Bermuda shorts have been a welcome addition to the rotation—the extra skin happily balancing out a very structured and fully covered turtleneck and blazer. I’m wearing sharp shorts by Róhe Frames and my blazer is an old +J Uniqlo two button style but any structured navy will do. The merino turtleneck by Cos, my shoes are Tory Burch, and the bag is The Row.

Everlane

oversized blazer

EVERLANE

Cos

merino wool turtleneck top

COS

Róhe

pleated tailored shorts

RÓHE

SHOBOP

Tory Burch

multi-buckle monk straps

TORY BURCH

Toteme

recycled-crepe shorts

NET-A-PORTER

SSENSE

Vince

low-rise pintuck shorts

SHOPBOP

Last month, mere seconds after Labor Day, I was invited to J.Crew’s “intimate” fashion week dinner for 500 guests at the New York Public Library. Given its scale you would have thought I would know someone else going well enough to text and ask what they were planning to wear. But I kept coming up short when asking friends if they were planning to attend. Panic set in, and I began to feel incredibly unsure of the dress code—technically a cocktail event, but hosted by the kings and queens of prep, and with no security blanket of a gaggle of work friends by my side. I wanted to feel appropriate and unique but, god forbid, overdressed. After trying on countless combos, my entire bed covered in clothing, I settled on a navy wool pair from the brand (sized up one size to get a good slouch!) and wore a button-down shirt, tucked in and some party heels. The shorts made me feel like I would be dressy enough among tuxes and slip dresses but not so gussied up that I wouldn’t fit right in should everyone have just come in what they wore all day. They ended up being…perfect.

Dôen

Hilla top

DÔEN

J.Crew

high-rise trouser shorts

J.CREW

Roger Vivier

metallic sequin slingback pumps

NEIMAN MARCUS

Sophie Buhai

Elegant scrunchie

SSENSE

The Frankie Shop

Wilma pleated bermuda shorts

THE FRANKIE SHOP

Weekend Max Mara

Nabulus wool bermuda shorts

LUISA VIA ROMA