How to wear shorts as a grown man and not look like you're in an Adam Sandler film

If recent red carpets are any indicator, we are living in a golden age of shorts.

A few years ago, the only celebrity to be seen wearing shorts in a professional context was Pharrell (unless you count pre-fame Timothée Chalamet, which I don't).

But in the past year, shorts – specifically, shorts paired with suit jackets – have started popping up everywhere. 

Red-carpet roll call

LeBron James wore a shorts/jacket combo to last year's NBA finals. Twilight star Robert Pattinson dressed in a Dior jacket and shorts at a recent premiere. And Nick Wooster, the ultimate menswear influencer, has begun pairing ultra-baggy shorts with suit jackets.

Meanwhile, New York designer Thom Browne – who offers suits with both three-quarter trousers and schoolboy shorts – has never been more popular: Harrolds says he's now one of the store's top-selling brands, and his company was recently sold for a cool $500 million.

Not even the impending Northern Hemisphere winter can slow down this trend: witness rapper-of-the-moment Tyler, The Creator, who got a shout-out from Vogue just last week for coyly donning khaki shorts on the red carpet.

A late bloomer

I suppose I should be celebrating this turn of events. You see, I am a grown man who wears shorts all year 'round, in all sorts of contexts.

I discovered shorts relatively late in life. As a precocious teenager, I always wore trousers, and as a twentysomething hipster, I favoured skinny jeans.

It wasn't until my late 20s that shorts became a fixture. Now, in my 30s, I wear shorts in all shapes and sizes, day and night. 


And yet, the current celebrity short trend is making me question my sartorial choices. 

What I've realised is that many of these celebrities look kind-of silly in their purposely mismatched attire. Am I making a fool of myself, too?

Words from an expert

I decided to phone a magazine-editor friend of mine for advice. He's the sort of guy who can wear an apricot-orange suit to a black-tie event and make it work, so I felt confident he'd know how to proceed.

I was mistaken. "Mate, I have no idea about shorts," he said. "I want to wear them, but I'm afraid I'll get it wrong."

If the most stylish person I know finds the shorts question confusing, what hope is there for the rest of us?

That's when it hit me.

It's all about confidence

The reason celebrities can get away with wearing shorts to formal events is because they believe in themselves. They understand that the act of wearing shorts is a bold statement, but they have the confidence to pull it off – even if it looks objectively stupid.

So, I've decided to keep wearing shorts to business lunches and meetings, but only on days when I feel like a million bucks. It's all about the confidence.

If you, too, are planning to wear shorts formally, there is one helpful piece of advice that my editor friend shared with me: match the fit of your top and your shorts.

The reason LeBron looks so good in his Thom Browne getup is because both the top and bottom halves are expertly tailored and slim-fit.

By contrast, Robert Pattinson looks rather shabby in his regular-fitting jacket and super-baggy shorts. It's as though he's just thrown on whatever he had lying around.

That's the long and the short of it.

Take a look at the gallery up top for our picks of adult-friendly shorts to rock this summer.

Dan's writing on style, travel and more has appeared in The New York Times, the Australian Financial Review, Condé Nast Traveller and others. He is based in Sydney.

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