The Right Shoes To Wear With Shorts

Nothing shows off your footwear like a bare pair of legs, so use these reliable combos anytime you put your shorts on

They say you can tell everything 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.

There’s a lot that can go wrong when you’re pairing new shoes and bare legs, so avoid any unsightly clashes with these foolproof shorts and footwear combinations.

Tailored Shorts
Smart but versatile, tailored shorts can be dressed up or down to suit the occasion and make the 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, Oxfords and Derbies all work 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, but still keep you looking suave.

Of course, these styles will only look sharp provided their 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 really spikes, classic leather sandals (nothing too Gladiator) 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.

Jersey/Athletic Shorts
With sports luxe and streetwear influences dominating 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 runners to slip-on canvas plimsolls and high-tops, almost everything works.

A pair of minimal low-top trainers in black, white or gray is probably the safest style to settle on if you’re prioritizing 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 aesthetic 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 selvage shorts with most of your casual shirts, tees and vests, what are the guidelines when it comes to footwear?

Keep it lo-fi. Designers and stylists might be re-imagining denim lately, even working it into eveningwear options, 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 (Chuck Taylors being the obvious option), minimalist sneakers, plimsolls or skate-inspired slip-on 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 silhouette, but there’s something unmistakably sharp and gentlemanly about a boat shoe that means you can sport them for slightly more formal events. If you think they’ve become a bit TOWIE in recent years, we wouldn’t necessarily argue. Just swap them out for some suede loafers.

Minimalist trainers offer the same flexibility with dress codes, so they’re a good option if you have day-into-evening plans. Or if you want to smarten your lookup, opt for suede or leather brogues, Derbies, drivers or leather sandals, 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 too many of us mislabels as ‘autumn/winter only’. Boots can work with shorts, especially if you opt for suede versions in lighter colorways, 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 after you get out of the water. If you’re not straying far from the pool or the beach, then flip-flops are fine. (Notice this is the only time they appear in this article. That’s not an accident.) Wear them or sliders for lazy days of swimming and sunbathing – 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, we’re going to have to insist on an upgrade. 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 swimming shorts (think muted colors or subtle patterns, not 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…

General Tips

Short Legs
If you’re a shorter gentleman, opt for low-profile footwear silhouettes (nothing above ankle height) with a good sole or slight heel in shades that are similar to your skin tone – all of which will combine to produce the illusion of height and longer legs.

When it comes to your shorts, go for a pair that finishes around mid-thigh or gives the hems a couple of folds to emphasize leg length.

Long Legs
On the opposite end of the spectrum, if you have long legs, opt for footwear styles that have a slightly higher profile. Desert and chukka boots, along with slightly chunkier trainers, brogues and Derbies, would be ideal.

Similarly, your shorts should finish on or just above the knee, in order to break up your vertical lines lower down and reduce the amount of skin that’s on show / being burned.

Exposed Feet
If you intend to bare your feet in a sandal or flip-flop this summer, make sure they don’t look like gnarled tree trunks. That means getting a professional pedicure (no shame in it, Frodo), or doing a bit of DIY grooming in the comfort of your own home.

At the very least, your toenails should be neat and clean, get rid of unsightly hard patches of skin, and if you really do look like a hobbit in the heat, consider trimming excess hair.


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