The Best Dress Shorts for Men Do All the Work for You
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Dress shorts, we'll grant you, used to be a bit of an oxymoron. These days, most of your favorite pants are readily available in summer-ready form: khakis, sweats, hell, even jeans . And yet, the specific type of breezy capital-T Trousers all over the runway—and on the shelves of your local big-box brand—haven't 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. That's 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 working in fashion today: 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 or loose layers. 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 Single Sparkle
- The Best Dress Shorts Overall: COS Tailored Drawstring Linen Shorts , $120
- The Best Budget Dress Shorts: Gap Linen-Cotton Shorts , $60 $41
- The Best Upgrade Dress Shorts: Todd Snyder Tropical Wool Tab Short , $228
- The Dressiest Dress Shorts: Stòffa Plain Front Washable Short , $475
- The Best Pleated Dress Shorts: Polo Raph Lauren Relaxed Fit Pleated Twill Short , $198
- The Best Dress Shorts for Fashion Guys: Auralee Light Wool Gabardine Short , $505
- The Best Linen Dress Shorts: Alex Mill Pull On Field Short , $150
In This Guide
- More Dress Shorts We Love
- How We Test and Review Products
- How We Make These Picks
Best Dress Shorts Overall: COS Tailored Drawstring Linen Shorts
Tailored Drawstring Linen Shorts
$120.00, COS
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 both the smart and summery ends of your closet.
The drawstring waist gives them a slightly more relaxed feel, but these would still work perfectly with an unstructured linen jacket, or a gently oversized shirt. To make them feel smart enough for summer cocktails, wear them with a pair of Derbys and black socks. Hey, if you’re feeling particularly “menswear”, you could even swap in a pair of backless loafers.
Best Budget Dress Shorts: Gap Linen-Cotton Shorts
8" Linen-Cotton Shorts
$60.00, Gap
If you don’t want to spring for a fully tailored pair, it’s best to keep it simple. Look for something flat-fronted, mid-length, and made from linen, and you’ll be unlikely to go wrong. 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 Tropical Wool Tab Short
7" Tropical Wool Tab Short
$228.00, Todd Snyder
Boasting a 7-inch inseam, this is one of the shortest 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.)
This pair also has the option of a matching tailored jacket, which is cut to a generous, slightly boxy fit. And even if you don’t spring for the jacket, we’d recommend following the same principle – look for more relaxed shapes up top, to keep the look modern. Just make sure that the length of your top doesn’t extend past the hem of your shorts.
Dressiest Dress Shorts: Stòffa Plain Front Washable Short
Plain Front Washable Short
$475.00, Stòffa
At the upper end of the dress shorts echelon sits this pair, from the reliably elegant New York brand Stòffa. Made in a mix of cotton and linen, they’re cut to a shorter, wider shape, which gives them a roomier fit around the thigh. In practice, it means they’ll look that much fancier than a regular pair of shorts – especially as they’re finished with an attached belt.
Stòffa is known for considering even the smallest details of its products, and this pair is no exception. You can even select up front how you’d like the brand to hem them for you. For what it’s worth, we’d recommend the plain hem, to match their minimal design.
Best Pleated Dress Shorts: Polo Ralph Lauren Relaxed Fit Pleated Twill Short
Relaxed Fit Pleated Twill Short
$198.00, Ralph Lauren
Generally with shorts, it’s best to look for design details that are rooted in classic menswear, to avoid them looking over-designed. (After all, the whole point of shorts is to look breezy.) This Polo Ralph Lauren pair is a perfect example of how to incorporate a little sartorial flair: Their double front pleats and side adjusters give them the flavour of classic styles from the 1940s. As such, they carry a sophistication that makes them a perfect choice for semi-formal summer parties.
Slim fit tees, linen shirts, and even a summer blazer would all partner well here. As for footwear, we’d stick to the classics: a pair of Weejuns or leather sandals if you’re going smarter, or canvas plimsolls if not.
Best Dress Shorts for Fashion Guys: Auralee Light Wool Gabardine Short
Light Wool Gabardine Short
$505.00, Mohawk General Store
Arguably, no-one makes (or wears) shorts like the Japanese. Auralee, in particular, has mastered the balance between stylish and relaxed that every great pair of shorts needs. If you prefer baggier pants and avoid anything too slim-fit, this should be the pair for you.
The added benefit of a longer length? They’re easy to smarten up. While running errands, you could wear these with Chucks and a baggy tee – but for drinks, swap in a pair of leather shoes, throw over a striped button-down, tidy up the beard, and you’re all set.
Best Linen Dress Shorts: Alex Mill Pull On Field Short
Pull On Field Short
$150.00, Alex Mill
An often under-appreciated element of summer dressing is that it needs to feel as low-effort as possible. Who wants complicated clothing in hot weather? With that in mind, a pair of pull-on linen shorts is about as low-fuss as it’s possible to get, while still looking smart.
It helps that this pair, from US brand Alex Mill, is designed with enough polish to do the hard work for you: the flax linen gives texture and surface interest, while the patch pockets make them feel more ‘designed’. Wear them with almost any of your summer shirts, and feel good about making no more effort than that.
More Dress Shorts We Love
Safi Short
$150.00, Casatlantic
Patchwork Shorts
$730.00, Dover Street Market
Borrowed Shorts
$365.00, SSENSE
Relaxed Shorts
$760.00, Margaret Howell
Martingale Virgin Wool Shorts
$1090.00, Nordstrom
Classic Short in Vintage Stripe
$270.00, Mohawk General Store
Tailored Wool Shorts
$725.00, Dries van Noten
Kogai Short
$295.00, Mohawk General Store
How We Test and Review Products
Style is subjective, we know—that’s the fun of it. But we’re serious about helping our audience get dressed. Whether it’s the best white sneakers , the flyest affordable suits, or the need-to-know menswear drops of the week , Single SparkleRecommends’ perspective is built on years of hands-on experience, an insider awareness of what’s in and what’s next, and a mission to find the best version of everything out there, at every price point.
Our staffers aren’t able to try on every single piece of clothing you read about on Single Sparkle(fashion moves fast these days), but we have an intimate knowledge of each brand’s strengths and know the hallmarks of quality clothing—from materials and sourcing, to craftsmanship, to sustainability efforts that aren’t just greenwashing. Single SparkleRecommends heavily emphasizes our own editorial experience with those brands, how they make their clothes, and how those clothes have been reviewed by customers. Bottom line: Single Sparklewouldn’t tell you to wear it if we wouldn’t.
How We Make These Picks
We make every effort to cast as wide of a net as possible, with an eye on identifying the best options across three key categories: quality, fit, and price.
To kick off the process, we enlist the Single SparkleRecommends braintrust to vote on our contenders. Some of the folks involved have worked in retail, slinging clothes to the masses; others have toiled for small-batch menswear labels; all spend way too much time thinking about what hangs in their closets.
We lean on that collective experience to guide our search, culling a mix of household names, indie favorites, and the artisanal imprints on the bleeding-edge of the genre. Then we narrow down the assortment to the picks that scored the highest across quality, fit, and price.
Across the majority of our buying guides, our team boasts firsthand experience with the bulk of our selects, but a handful are totally new to us. So after several months of intense debate, we tally the votes, collate the anecdotal evidence, and emerge with a list of what we believe to be the absolute best of the category right now, from the tried-and-true stalwarts to the modern disruptors, the affordable beaters to the wildly expensive (but wildly worth-it) designer riffs.
Whatever your preferences, whatever your style, there's bound to be a superlative version on this list for you. (Read more about Single Sparkle's testing process here .)
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