You’ve probably had denim shorts in your closet since you first took a pair of scissors to tired jeans in junior high. At this stage, they’re reliable classics—which is not the same thing as boring. With some thoughtful styling and pitch-perfect footwear, jean shorts can be the quiet star that anchors your favorite weekend looks this season.
1. Upgrade a Basic Button Down
When pairing an oversize oxford shirt with raw-hem jean shorts, the half-tuck is the instinctive move. But letting those shirttails hang loose is actually the key to making this your new warm-weather uniform. A thin belt lends structure and slims the silhouette, while a crisp, structured purse further offsets the slouchy fit, cool-girl cuffed sleeves, and casual shorts. The crowning touch: elegant slip-ons in an understated pattern that go with absolutely everything.
2. Give Sporty Some Structure
Athleisure combo you’ve never thought to try: slouchy blazer + a soft, I’d-wear-this-every-day-if-I-could hoodie. See how the classic jacket, simple jewelry, and office-ready handbag transform loose denim and a cozy sweatshirt into a street-style masterpiece? Pull in a pop of color with a demure low heel.
James Perse Cotton-Blend Jersey Hooded Top, $225, netaporter.com; Topshop Moto Ashley Boyfriend Shorts, $55, topshop.com; DKNY Oversized Blazer, $398, farfetch.com; Aquatalia Melanie, $475, aquatalia.com
3. Play With Proportions
Sculptural tops stormed the runways this season, and we’re obsessed with the proportions of this one: a high neckline and voluminous sleeves billowing from a sexy crop. To keep the proportions in check, pair a statement-making shirt with classic double-cuffed denim shorts (no messy fringe in sight) and a belt bag that doesn’t interfere with everything you have going on up top. As always, a few choice accessories tie things together: Oversize sunnies and pretty heels with rich details give the whole look chic, art-school vibes.
Tibi Corset Knit Sculptes Hoodie, $595, tibi.com; Current/Elliott The Boyfriend Distressed Denim Shorts, $200, netaporter.com; Lauren Ralph Lauren Winston Belt Bag, $58, macys.com; Aquatalia Natalia, $495, aquatalia.com
4. Go Wild
All denim shorts needn’t be short shorts. Check out this perfectly threadbare pair, which hits at the more conservative mid-thigh. Then notice how the demure length plays nice with this high-necked blouse for gone-on-safari Out of Africa vibes. Keep the accessories modern with a structured yet streamlined purse and scooped-out booties—a playful twist on the suede staples everyone wears.
Equipment Rory Patch-Pocket Silk Shirt, $247, matchesfashion.com; Madewell Distressed Denim Shorts, $70, netaporter.com; Sara Battaglia Lucy Cara Cross-Body Bag, $929, farfetch.com; Aquatalia Filomena, $495, aquatalia.com