There was a time when a pair of shorts fell into one of two camps: tailored and trim or technical and sporty. And sure, both still have their place. But this summer, the silhouette has relaxed considerably. The prevailing mood for 2026 is fuller, slouchier and just a little louche—often with a pleated front, a roomier leg and enough drape to move with some swagger. There’s an air of Riviera elegance that allows you to look both at ease and stylish as hell.

Think of that now legendary street style photo of the late, great Giorgio Armani. The designer was snapped in a monochrome navy fit—sweater draped over shoulder with shades and some well-worn loafers—talking into a chunky ’90s cell phone. It’s the kind of effortless ease menswear keeps circling back to: relaxed without looking sloppy, refined without trying too hard. The proportions do most of the work for you. The good news is you don’t need a designer archive or a Milanese pedigree to pull it off.

Brands at every price point are embracing the baggier short, offering versions in crisp cotton, washed linen, airy wool blends and even updated technical fabrics. Whether you lean minimalist or more fashion-forward, there’s a pair out there ready to replace your too-tight summer staples.