Lookbook
Daytime Boxer Shorts with Oversized Poplin Shirts
A bold streetwear-resort crossover styling poplin boxer shorts as intentional casual daytime wear. Playful Bengal stripes, elasticated waistbands, and oversized unbuttoned shirts exude laid-back Mediterranean confidence. Crafted for hot summer city weekends, poolside cafes, and beach boardwalks.
$87
Beige Crochet Camp Collar Shirt, Striped Shorts, and Canvas Sneakers
5 pieces · Oct 27, 2026
Shop pieces for these looks
$101
Black Boxy Crewneck T-Shirt with Olive Striped Shorts and Fisherman Sandals
4 pieces · Oct 27, 2026
$109
Navy Linen Chore Jacket with Red Striped Boxer Shorts and Leather Slides
4 pieces · Oct 27, 2026
Shop pieces for these looks
We assembled this edit to embrace high-fashion's playful adoption of cotton boxer shorts for summer daytime dressing. Pairing crisp striped boxers with billowy linen overshirts and leather slides transforms loungewear staples into an intentional resort statement. Ensure outerwear remains generous and structured to balance the relaxed leg exposure. Our editors suggest accessorizing with woven leather totes and dark sunglasses to ground the relaxed resort silhouette with urban intentionality.
— The Editors
All curated searches
12 of 36- Men's Blue Striped Seersucker Swim Trunks
- Men's Brown Suede Buckle Slide Mules
- Men's Dark Brown Woven Leather Tote Bag
- Men's White Linen Long Sleeve Shirt
- Men's White Ribbed Cotton Tank Top
- Men's Brown Leather Strap Dress Watch
- Men's Brown Woven Leather Loafers
- Men's Leather Bound Reading Book
- Men's Oatmeal Ribbed Crewneck Sweater
- Men's Striped Seersucker Shorts
- Men's Tortoiseshell Frame Sunglasses
- Men's White Crewneck T Shirt
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