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The Summer Guide to Wearing Shorts

Free your knees with full confidence this season

By: The Harry Rosen StaffDate: 2023-06-15

Once the mercury rises past a certain point, persisting with pants extends beyond all practical sense. While many men routinely reinforce their “not a shorts guy” statuses at the onset of each summer, the undeniable alure of shedding into shorts eventually proves too difficult to ignore. So, why try to fight the inevitable? We suggest caving-to and embracing your natural desires — after all, there’s only a few months of summer every year, and they’re designed for uninhibited pleasure. Here’s our guide on how to rock a pair of shorts this season.


Time and Place

Outside of your athletic endeavours, gaining a good understanding of when to wear a pair of shorts is half the battle to pulling them off. Obviously, a great time to start is when it’s simply too hot out to wear anything longer. That said, there certainly are scenarios that warrant wearing shorts more than others.


At the beach, on a sunny vacation, at the cottage, on the weekend; these are all opportune times to wear shorts. On an airplane, at the movies, on the subway, in a restaurant; these are all places to avoid wearing them. Overly air-conditioned areas are the natural-born enemy for shorts, and as such should be swerved whenever possible.


Length

They aren’t called ‘shorts’ for nothing. That said, inseams seem to be the major sticking point for those with any apprehension about pulling on a pair. While differing lengths come in and out of fashion, too short or too long are both extremities you should avoid.


If your inseam falls anywhere within the 5” - 9” range, you’re doing well. Whether you prefer yours on the shorter or longer end of that spectrum is entirely up to you, but if you venture outside that territory, you’re swimming at your own risk.


Fabric

The material your shorts are made of also makes a big impact, both visually and performance-wise. Selecting certain fabrics over others is paramount to keeping you comfortable during summer’s hottest days. We prefer quintessential summer fabrics like linen, seersucker, silk-blends, or lightweight cotton.


Technical fabrics, although ideal for your athletic endeavours, tend to look out-of-place when paired with casual clothes. Your running shorts might look great with your gym gear but they’re not going to look as smart when styled with a laid-back button-down.


Stylistic Details

Once fit and fabric are taken care of, all that’s left to do is decide which stylistic elements you want your shorts to feature. If these are meant for everyday wear, then a regular flat-front cotton pair with slash side pockets and traditional chino details are your best bet. But you can find styles to help you dress up or down.


Substitute belt loops for side adjusters and add a tab to your front button closure: you’ll have a smarter pair of shorts that more closely resemble tailored trousers and consequently can be worn with more formal outfits.


Or, if your day-to-day get-up is more on the casual side, switch things up with a drawstring closure or elastic waistband. Cargo pockets, when tastefully executed, can also enhance a pair of shorts’ casual sensibilities, though are classically unfashionable when baggy and below knee-length.