The Right Shoes To Wear With Every Type Of Shorts This Summer

They say you can tell a lot about a man by his shoes. If that’s true, summertime is when you really lay yourself bare because, in shorts, your choice of footwear is almost as glaring as your sunburn.

More than just what type of shoe to wear, you have to consider if they go with the style of shorts you have chosen, which in turn should go with whatever’s on your top half and all of which should go with wherever you’re wearing the lot.

In short, and in shorts, there’s a lot that can go wrong when pairing new shoes and bare legs. To avoid any unsightly clashes this season, follow these foolproof shorts and footwear combinations.

Tailored Shorts

Smart but versatile, tailored shorts make for an ideal warm-weather alternative to formal trousers at smart-casual events such as garden parties and wedding receptions.

The rule to remember here is that smart shorts should be paired with an equally smart shoe, so team tailored shorts with your more refined footwear. Brogues and Derbies work particularly well, whether you opt for models in leather or seasonally-appropriate suede, while chic loafers and driving shoes in similar materials will add a more laid-back feel.

Of course, these styles will only look sharp provided they’re worn sock-free. So, get up to scratch on going sockless before getting your hairy pins out. Suffice to say, you’re going to need some invisible shoe liners.

When the mercury spikes, classic leather sandals in navy, black or brown will maintain a sophisticated appearance; while scruffy canvas trainers, flip-flops or other decidedly casual styles only jar with the sharp, tailored cut of your (upper) legwear.

Athletic Shorts

With sports luxe and streetwear influences dominating fashion trends for the past few years, jersey, nylon and other sports-inspired shorts have become a comfortable failsafe for those that like to dress down, not up.

If you’re a man of athleisure, you’ll want a shoe that offers the same degree of comfort and breathability. Which means trainers. From luxury designer takes and technical running shoes to slip-on canvas plimsolls and high-tops, almost everything works.

A pair of minimal low-top trainers in black, white or grey is probably the safest style to settle on if you’re prioritising versatility. Not only will they lend a sleek edge to your shorts – stopping it from looking like you’re always on your way to the gym – they’ll also act as a handy tool to dress down your suit when you want to put a casual spin on your tailoring.

Fans of the streetwear look can also consider pool sliders, especially when temperatures rise. Team them with white sports socks for a two-finger salute to conservative tastemakers, though don’t expect to get in any hotel bars. Even the ones with a rooftop pool.

Denim Shorts

Not just the preserve of grunge bands and Pride Week attendees, denim shorts are one of those items you can turn to in more situations than you might think. A hardy summer staple for holidays and weekends in the city, they’re a good option when you don’t want to think too hard about what to wear.

While it’s easy to style a pair of selvedge denim shorts with most of your casual shirts, tees and vests, there are guidelines to follow when it comes to footwear. Chiefly, keep it lo-fi.

Designers and stylists might be re-imagining denim lately, but the fact remains that denim cut-offs are unquestionably casual. And unlike sporty styles, they have a little more of a grunge-inspired kick to them, so footwear that’s fuss-free and fashionably offbeat is the way to go.

Try teaming with canvas trainers, minimalist sneakers, plimsolls or skate-inspired slip-ons for easy off-duty looks, switching for a pair of espadrilles if you plan on taking your denim to the coast.

Chino Shorts

Unbeatably versatile, a pair of chino shorts is an indisputable summer wardrobe staple. Straddling the line between smart and casual, there are few footwear styles that don’t play well with chinos.

For a classic pairing that works for almost any warm-weather situation, team them with boat shoes. Yes, it’s a casual shoe, but there’s something unmistakably sharp about them that means you can sport them for slightly more formal events. For something more commonplace on land but with the same Riviera vibes, swap them out for some suede loafers or even leather brogues or Derbies, which will highlight your shorts’ tailored look rather than the relaxed chino fabric itself.

Another silhouette that might not immediately spring to mind is the desert boot – something most wrongly mislabel as ‘autumn/winter only’. Boots can work with shorts, especially if you opt for suede versions in lighter colourways, which will add a rugged yet polished feel to your outfit.

Alternatively, if you’re hitting the beach or hanging by the pool, espadrilles and sandals work just as well to keep your summer style on-point. We told you chinos worked with anything.


How you pair your footwear with swim shorts depends a lot on what you’re planning on doing after you get out of the water.

If you’re not straying far from the pool or the beach, then flip-flops are fine. You can wear these or sliders for lazy days of swimming and sunbathing on account of both being better than getting athlete’s foot, or sand in your good loafers for that matter.

If you’re moving to a beach bar or restaurant, an upgrade is required. Flip-flops won’t do as soon as you step 10 meters off the beach. Sleek trainers, espadrilles or suede loafers dress up smarter styles of swimwear (think tailored cuts and muted colours or subtle patterns rather than your boardies). Just remember that if you’re heading to a restaurant, you will have quite a lot of leg on show. Maybe stick to somewhere with outside seating.