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
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
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
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
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.
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