Every summer, the men’s clothing conversation inevitably turns to shorts. How long (or short) should they be? Can you wear these to the office? What will happen at night? Should a man even wear shorts? All valid questions. A breezy pair of shorts may be practical and comfortable when the temperatures rise, but they’re not exactly known for indicating an advanced level of style. Or at least, that’s what conventional menswear wisdom suggests. However, these days, an increasing number of well-dressed men are taking issue with shorts can do Look charming and attractive—as long as you know what you’re doing.
In the summer, record-label executive Samir Sadhu has no hesitation in reaching for the shorts. He’ll wear them with everything from lightweight button-ups to gauzy white tees (and, occasionally, napalm death long sleeves). “These are things I have always worn,” says Sadhu, who grew up in the humid climate of Singapore. “Shorts and a T-shirt were kind of my uniform. As I got older, it got a little more sophisticated.” For Sage, that refinement meant swapping out his trusty Dickies for the sleek designs of Comme des Garcons and Stoffa. And just as important, it also meant upgrading what was on her feet: “Now I just wear loafers instead of a pair of Converse or Vans.”
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This sentiment came up again and again in my interviews: the transformative power of a great leather shoe. “The key ingredient for me when elevating a pair of shorts is reaching for a pair of loafers,” says fashion writer Jake Wolf. Menswear veteran Nick Wooster agrees – in fact, he argues that some well-worn summer loafers are far more versatile than a pristine pair of sneakers. “If you’re wearing shorts with sneakers, you’ve pretty much put yourself in a box,” says Wooster. “It’s very hard to get out of that.”
From there, the supporting details matter just as much. Wooster points to a hierarchy of attire: A button-up shirt is naturally more dressy than a T-shirt, while a blazer feels more dressy than a sweater. “It doesn’t have to be expensive,” he says. “I treat a tailored jacket the same way people treat a cardigan or overshirt. It’s just something to wear.” His second trick is what he calls the “sartorial mullet” – business on top, party on the bottom. As Wooster says, “Something dressed up with something super casual instantly makes it cool.”
Whether you’re wearing a T-shirt, button-up, or pique polo, Wolf suggests tucking your top instead of letting it hang loose, which gives your outfit a neater look. Adding some well-styled accessories – a carefully selected belt or some attractive shades – will only enhance the look. “It’s all about showing intent,” he says. “All these things help make it feel a little more attractive.”
