Dress shorts used to be hard to find. Even as most of your favorite pants—khakis, sweats, hell, even jeans—became readily available in summer-ready forms, the specific type of breezy capital-T Trousers all over the runways these days rarely had much in the way of warm-weather counterparts … until now.
This is a huge relief: If you’re going to lunch on vacation, or spending the day at a beach club, or if you’ve got friends with a place upstate (lucky you), you’re really going to need a pair of shorts that weren’t made for the gym. This is where the best dress shorts for men come in.
As for how to wear the style, there are two paths to take, best embodied perhaps by two of the most stylish men in recent fashion history: Thom Browne and Rick Owens. The Thom route is neatly tailored with an abbreviated fit, designed to be worn with a button down or classic sweatshirt. The Rick route is more oversized, less structured, and cut to a longer length, to wear with tees and looser button-ups. Either way, you don’t want anything too tight: nothing undermines a dressy look faster than the sight of a visibly straining seam. As for fabrics, don’t overthink it. Cottons, linens, and lightweight wools are stalwarts for a reason.
The Best Men’s Dress Shorts, According to GQ
Best Dress Shorts Overall: COS Tailored Linen Shorts
As a general all-rounder, this pair is hard to beat. Made by COS (the better made, dare we say better designed offering from the H&M group), it ticks a lot of the boxes you’ll need from a pair of smart shorts: a fit that’s tailored but not clingy, a lightweight and grown up fabrication, and a colour that’ll pair well with the smartest end of your closet.
The linen gives them a slightly more relaxed feel, but their color means these could still work perfectly with an unstructured jacket or a gently oversized shirt. And don’t let the black conjure up memories of restrictive school uniforms—this time, there’s some comfortable elastic in that waistband.
Best Budget Dress Shorts: Gap Linen-Cotton Shorts
If you don’t want to spring for a fully press-creased pair like the one above, look for something flat-fronted, mid-length, and—especially this time of year—made from linen. This affordable example comes from GAP, but squint and they could be made by a contemporary Scandi brand.
They sit a little lower on the waist, which should influence your choice of clothing: Make sure a T-shirt, polo, or button-down is long enough to cover the belt loops, or you’ll risk an unsightly sliver of belly showing. Whatever you choose, leave it untucked, or French-tucked, to avoid looking like a Boy Scout.
Best Upgrade Dress Shorts: Todd Snyder Cotton Side Tab Short
Boasting a 7-inch inseam, this is one of the shorter options on our list, so it’s perfect for those wanting to show a little more leg. For what it’s worth, Prada revived short-shorts a couple of years ago, and they’ve steadily regained popularity with menswear heads who are bored of baggier clothes. (If you’ve got the thighs for them, we’d advise going for it.)