Cool and crisp, the boxer short trend seems to get a reboot every few seasons. One might say it peaked last summer, when cotton poplin styles were ubiquitous in TikTok outfit diaries thanks to their inherent gender-neutral appeal that allows for diverse styling that could pass as both high-fashion and street-friendly. The boxer short has been the menswear-inspired look since 2022, when Miu Miu sent shorts and miniskirts down the runway with exposed underwear peeking out from ultra-low waistbands reminiscent of aughts fashion. Bottega Veneta and The Row brought their own vision for how to wear the trend during their fall and pre-fall 2023 collections, respectively: with a matching shirt only half-buttoned to show a flash of skin (and the elastic waistband) with a structured blazer and leather flip-flops for an Olsen twin-approved business casual look. Bella Hadid, Alexa Chung, and Kendall Jenner were early adopters, followed more recently by Taylor Swift, who gave it a preppy spin by pairing her blue pinstripe boxers with a relaxed button-up and pointy pumps during her promotion tour.
The boxer short trend remains relevant right now—Vogue recently declared “men’s boxers as one of biggest menswear trends in women’s fashion,” though one could argue there’s no better time to give the underwear-as-outerwear look a try than right now. Peak warm weather calls for the least amount of clothing possible, and cotton poplin shorts are a functional wardrobe staple that offers just enough coverage to stay cool with a hint of cheeky style. Below, we’ve mapped out seven ways to help you bring the look to life this summer: you can make it feel romantic, fashion-forward, sporty, beachy, preppy, or just downright easy—the beauty of the boxer short trend is its fluidity, after all.
The Pinstripe Boxer With a Mesh Flat and Prairie Girl Top
Zara’s dainty blouse adds feminine charm to blue pinstripe boxer shorts. Style a perfectly tailored pair with Ulla Johnson’s woven basket bag and red mesh flats that play off the basket’s colorful woven pattern. Marie Lichtenberg’s wrap-around rope necklace brings an element of island time to wherever you are.
The Logo Waistband Style With a Crochet Shirt and Kitten-Heeled Sandals
Dress up Hommegirls’s tiny boxer short with a Calle del Mar crochet cover-up and kitten-heeled sandals—Khaite’s will have near-endless mileage in your wardrobe. Metal-rimmed shades from Celine and a raffia bucket hat from Jacquemus are practical yet fashion-forward accessories, while Staud’s laser-cut flower bag gives summer blooms a whole new meaning.
The Classic White Boxer With a Matching Button-Down and Cool-Girl Sneaker
For a preppy-meets-sporty look, pair a white boxer with a matching button-down shirt. Keep the rest of your ’fit casual-cool with comfy Veja sneakers, Gucci’s retro shades, and Dragon Diffusion’s black leather tote. Tie a silk scarf around the handle or in your hair for a feminine touch.
The Striped Boxer With a Colorful Bikini and Fashion Flip-Flops
Beach-bound? Try a little bikini with Solid & Striped’s blue boxer short. A wicker bag and floppy hat complete the look, while a patterned scarf can double as a chic top for a post-dip lunch on the deck.
The Colorful Boxer With a Baby Tee and Jelly Flat
All the cool girls are wearing jelly shoes! And Pointelle tops! Give both trends a try with Ancient Greek Sandals’s water-friendly pair and Coucou Intimates’s baby tee—two perfect mates for Comme Si’s green-striped shorts. Tory Burch’s mesh tote and Loewe’s retro-inspired shades give an extra personality wink.
The Tiny Boxer With Beachy Jewels and Mary-Janes
Embrace that carefree summer energy with J.Crew’s purposefully wrinkled cami, Dôen’s blue-and-white shorts, and Julietta’s beaded seashell pendant—handmade in Brooklyn and inspired by vintage jewelry. Aeyde’s Mary Jane keep the look city-friendly, while a day clutch from Hunting Season offers a nice alternative to carrying a big shoulder bag.
The Longer Boxer With a Knit Polo and Fisherman Loafer
Channel Nancy Meyers-esque coastal living with The Frankie Shop’s navy and cream short and Emme Parsons’s fisherman sandals. Add in texture with a knit polo from Sea and Miu Miu’s nautical-inspired tote. A red, white, and blue rope pendant from Ben Shoppe ties it nicely together.
