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What goes with what

Stress-free shorts and shoes combinations

Stress-free shorts and shoes combinations

There is something about shorts that sends even the most sartorially savvy man into a bit of a tailspin. But, whether you love it or loathe it, the season for shorts is here. So, other than making sure your knees and calves are fit to be seen, what should you be thinking about?

Well, shoes for one. The shoes and shorts combo feels like an obvious one – just put some shorts on add some shoes and you’re good to go. But, like shorts and shirts there are ways to make more of an impact.

The rules around shorts are constantly shifting. A few years ago you couldn’t wear them in the office. Now, dress code permitting, you can. That being said, it’s worth sticking to one or two guidelines to make it easier for you.

“Try to keep them around an inch above the knee. No higher unless you’re on a beach wearing swimming trunks,” says stylist Freddie Kemp. And while baggier, casual shorts are popular again for day-to-day, avoid anything oversized that comes past your knees. “They can make you look shorter unless you’re an NBA Basketball player.”

These guidelines – not rules – apply to footwear combos too. “You don’t have to match like for like, but it does make it easier to get ready and know what looks good when you keep similar style items together, like chino shorts with boat shoes,” says Freddie.

However, you shouldn't feel limited to only wearing boat shoes or loafers with chino shorts and only wearing trainers with sports shorts. “Your shorts and shoes are part of your whole outfit, so there is room to play around with different colours and patterns.”

This doesn’t mean you need to grab your loudest patterned shorts and brightest t-shirts, but it does mean you can experiment with colour. “A bright pair of shorts works really well when worn with neutral colours. And if you go for an interesting fabric like corduroy or linen, it looks intentional rather than like you’re still wearing your holiday gear,” says Freddie. Anything goes when it comes to thinking about shorts and shoes, but some combinations are easier than others. “A sandal or loafer is the default footwear when it comes to shorts, as they're the easier styles to wear. They elongate your legs because there’s nothing between them and your shorts to break the line of vision,” says Freddie.


If sandals aren't your thing and you don't want to spend the summer wearing formal shoes, then consider the humble trainer. Canvas feels summery and lets the foot breathe more than a traditional pair of kicks.

If you want to push the style boat out a bit, then try trainers with visible socks, especially if you’re going for a more casual look. “I love the effortlessness you get from trainers. Hi-top trainers feel fresh and modern but they can be trickier to pull off because they go higher up the leg,” says Freddie, “A way to combat this is to keep your shorts on the higher side of appropriate and a more casual material. Anything too formal, like tailored shorts with hi-tops, starts to feel very fashion-y at best and like a mistake at worst.”

Whether you opt for the classic shorts and sandals combo or mix it up, it's worth trying a few different styles. After all, shorts season only comes once a year.


Words: Nadia Balame-Price
Photography: Jamie Stoker
Styling: Freddie Kemp
Styling assistant: Toby Standing