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The Knack

The Best Shoes To Wear With Shorts

How to choose the right footwear when baring your legs

Once upon a time, the only thing a man worried about when pulling on a pair of shorts was how white his legs were, or maybe how knobbly his knees appeared. But now that shorts have become a summer wardrobe essential and can be worn in a business meeting as well as on the beach, you need to think carefully about how to match the right style with the right shoes for the right occasion.

As a general rule of thumb, the more casual the cut, the more relaxed the shoe, but you might also want to take the length and colour of your chosen shorts into consideration to ensure you get the right combination. (You can read more about that here.)

Here are our five favourite footwear styles for summer and the shorts that work best with them. 

Boat shoes

Perfect for: casual weekends with friends

Boat shoes are perhaps the most adaptable of summer footwear. They were created by Mr Paul Sperry of Connecticut in 1935 when he cut siping (a series of narrow slits) into the rubber soles of his shoes to prevent them slipping on a wet deck. His Top-Sider style is still essential kit for fair-weather sailors today, although the shoes are now, of course, just as at home on dry land.

Take inspiration from their sporting roots and keep things casual. Boat shoes work brilliantly with cool linen shorts cut to the knee. Look for a looser cut as this will allow any breeze to circulate and keep you cool. Boat shoes come in a huge range of colours, so they can also work well when paired with patterned shorts. For a New England style, look out for subtle embroideries or go tropical with bolder prints. Traditionally, the summer sailors of Nantucket would wear red shorts that would fade in the sun so boat shoes work well with shades of pink. If you prefer darker shorts, pair them with a pink polo shirt.

Boat shoes are designed to be kicked on and off, so ditch the socks completely. If you are wearing boat shoes in town, start the day by making sure your feet are completely dry after you shower and then lightly dust with talcum powder. You will thank us later.

Try these

  • Oliver Spencer Linen Drawstring Shorts

  • Sperry Authentic Original Leather Boat Shoes


       

Sneakers

Perfect for: sunshine city breaks

For weekends and holidays, denim shorts look great with sneakers. Forget “Club Tropicana” cut-offs. Jean shorts work best when tailored to fit closer to the leg, though not so tight that they constrict your thighs – this will be uncomfortable in hot weather to say the least – and ending just above the knee. Again, for reasons of comfort, look for shorts that sit on the waist to avoid them riding up and causing, ahem, any problems down below.

While denim shorts look good when faded, for a more polished style, pair white sneakers with darker flat-fronted chino-style shorts. Navy and white is a classic summer combination. Sneakers aren’t designed to be worn barefoot, so if you want to bare your ankles invest in invisible socks. Sneakers also work well with ankle-length sports socks, but be aware that while you gain in comfort you might end up with an unfortunate tan line if you are in the sun all day. For a sockless alternative, go for a knitted sneaker.

Try these

  • NN07 Slim-Fit Washed Stretch-Denim Shorts

  • Converse 1970s Chuck Taylor All Star Canvas Sneakers


        

Loafers and driving shoes

Perfect for: relaxed balmy evenings eating out in town

If you favour pleats and turn-ups on your shorts, a classic chino cut pairs perfectly with loafers and driving shoes, particularly if the latter are suede. Chino shorts come in any number of colours, but perhaps look best in all-American shades of tan and stone. This style works well if you prefer to tuck your shirt into your trousers and can be twinned with a chambray button-down shirt for work. You can wear a knitted or club-stripe tie if needed. Don’t forget to wear a belt, however. A woven one is nonchalant but still suitably stylish. The best accessory, however, is a pair of tanned calves, so remember to slap on the appropriate SPF sun cream every day to protect and moisturise your legs.

The leather uppers of a loafer or driving shoe can stick uncomfortably to your feet in the heat so, as well as wearing no-show socks, you might want to dust the top of your feet lightly with talc to keep your skin dry. 

Try these

  • Rubinacci Manny Pleated Stretch-Cotton Twill Shorts

  • Tod's Gommino Leather Driving Shoes


        

Lace-ups

Perfect for: summer days in the office

The advent of city shorts has meant that lace-ups have found a new summer role, although the gentlemen of Bermuda have been wearing them with shorts for years. Black Oxfords won’t work, but rubber-soled brown brogues can look great. If you are looking for something lighter, styles in woven burnished leather or hand-coloured raffia inspired by Sicilian fishermen are cool in every sense of the word.

Think smart and take inspiration from your suits, rather than your swim shorts. Your shorts should be tailored to the leg. You don’t want any unfortunate gaping or risk being nicknamed Plums by your colleagues from thereafter. Length-wise, they should finish just above the knee. Twin the shorts with a blazer or a blouson for an alternative to a suit jacket when the heat is on.

Classic Bermuda shorts are traditionally worn with long socks, but this does seem to defeat the object somewhat when it is roasting outside, so secret socks work perfectly. Don’t be tempted to tie your laces too tightly as feet tend to swell in the heat. Alternatively, go for good-quality fine lisle ankle socks in a light colour. Navy and black are difficult to pull off and white is a no-no if you’re aiming for a smart look.

Try these

  • Officine Generale Slim-Fit Cotton-Seersucker Shorts

  • Marsell Washed-Leather Derby Shoes


      

Sandals

Perfect for: beach bars or lunches on a terrace overlooking the ocean

When you’re after maximum exposure, twin short shorts with a pair of sandals. To dress them up, look out for a sharper style of leather sandal, and if you are going to be driving, consider a pair with a back strap so your feet don’t slip off the pedals.

If you don’t want to expose too much thigh, go for loose cargo shorts in linen blends and think casual with Birkenstock-style sandals. If you’re travelling and want to head straight to the beach after getting off the plane, a pair of longer, tailored Orlebar Brown swim shorts are perfect. Slides are great for air travel, too, because you can simply kick them off when you pass through security.

The old taboo of not wearing socks with sandals is well past its sell-by date – it’s up to you. If you prefer to go sockless, though, do consider having a pedicure. Ugly nails are never in style. And remember to spray insect repellant on your feet in the evening. Bites can rub uncomfortably against those sandal straps.

Try these

  • AMI Cotton-Canvas Cargo Shorts

  • Rick Owens + Birkenstock Arizona Leather Sandals