Shorts and Shoes

We live in an age where men take more pride in their appearance than perhaps ever before. However, for even the most hardened of sartorialists, there is still one garment of clothing that makes blood run cold at its mere mention.

Shorts have always been notoriously tricky to wear. Finding shorts and shoes combinations that really work is something that has eluded men since they first began caring. To get it right is to master one of menswear’s most challenging obstacles and breeze through the summer in style. To get it wrong, on the other hand, is to wind up looking out of sorts and confused until the heat eases off enough for you to pour yourself back into a pair of slim-fit jeans and breathe a sigh of relief.

Striking a sense of balance between your shorts and your shoes is what you should be aiming for. That means yes to athletic shorts with sports footwear and a big, fat no to brogues with swimming shorts. That much should already be obvious, but to make things even clearer, we’ve rounded up the shorts styles every man should own, a collection of foolproof footwear, and then combined them to create a selection of surefire looks to see you through every warm-weather occasion.

Key Types Of Shorts

As is the case with any item of clothing, there are certain types of shorts that are best given a wide berth if you’re to remain looking stylish. In order to avoid any confusion, these are the four key styles it’s worth having at your disposal.

Tailored

Drake’s Beige Cotton Shorts, £195 at DRAKE’S >
Incotex Slim-Fit Linen & Cotton-Blend Shorts, £190 at MR PORTER >

Contrary to popular belief, it is still entirely possible to head out for an evening meal on holiday and not look like you’ve just stepped out of the pool. The secret is tailored shorts. They’re essentially a pair of dress pants that end above the knee, and when paired with loafers or luxe sneakers, they’re a great way to stay cool and look put together all at the same time.

Chino

Beams Plus Ivy Chino Shorts, £115 at END CLOTHING >
A.P.C. Benjamin Shorts, £159 at END CLOTHING >

Chances are denim is your go-to legwear from autumn through to spring. But your jeans’ short-legged siblings are a lot more difficult to get right. Instead, a few pairs of chino shorts should form the backbone of your summer wardrobe – they’re comfy, they’re stylish and they look good with almost everything.

Sporty

French Terry Tracksuit Shorts, £25 at ARKET >
Reigning Champ Lightweight Terry Sweat Shorts, $95 at REIGNING CHAMP >

When comfort is key, athletic legwear is the only way to go. Training shorts are often crafted from highly breathable performance fabrics, which make them great for keeping cool in your downtime. Just ensure you team them with slightly smarter pieces so it doesn’t look like you’re always on your way to or from the gym.

Swimming

Orlebar Brown Navy Sport Swim Shorts, £95 at ORLEBAR BROWN >
Frescobol Carioca Pepe Tailored Swim Shorts, £160 at FRESCOBOL CARIOCA >

It wouldn’t be summer if you didn’t take the occasional dip or two, making a few good pairs of swimming shorts nothing short of essential. But that doesn’t mean digging out those tattered old boardshorts from the back of the wardrobe. Swimwear has come a long way and now it’s possible to secure something that will take you from beach to bar without even having to stop for a change.

Key Types Of Shoes To Wear With Shorts

Picking the shorts you’re going to wear is the easy part. It’s deciding what shoes to team with them that can cause problems. Get your shoes wrong and it can throw your whole outfit out of whack. But stick to these classics, match them with consideration, and you really can’t put a foot wrong.

Canvas

Chuck 70 Classic Low Top, £65 at CONVERSE >
Novesta Star Master, £49 at END CLOTHING >

Canvas trainers are arguably the ultimate summer go-to. They’re breathable, relatively lightweight and can be dressed up or down. A plimsoll like the Converse Chuck Taylor All Star 1970 or Novesta Star Master will make for a great day-to-day shoe. Meanwhile, a smart canvas slip-on is an excellent option for combining with tailored shorts in the evening.

Luxe Sneakers

Common Projects Taupe Suede Original Achilles Low Sneakers, £325 at SSENSE >
CQP Racquet Sneaker, £255 at TRUNK CLOTHIERS >

Sometimes it doesn’t matter how clean and white your canvas shoes are, they’re just not smart enough for the occasion. When that’s the case, a pair of luxe leather sneakers is always a safe way to go. They’re cool, they’re classic and they’re versatile enough to go with every style of shorts in your wardrobe.

Sandals

Miltos Crossover Leather Sandals, £110 at MATCHESFASHION >
Teva Original Universal Leather Sandals, £55 at COTSWOLD OUTDOOR >

When it comes to staying stylish abroad, a good pair of sandals is key. Flip-flops are all well and good, but invest your money into a sturdy pair of strapped sandals and you’ll find they’re comfier, more versatile and will last you several summers. Plus they look the business with a pair of tailored or chino shorts.

Sports Sneakers

Reebok Club C 85 Trainers, £64.99 at OFFICE >
Nike Air Vortex Suede And Mesh Sneakers, £75 at MR PORTER >

Sports sneakers are another footwear style that will combine well with anything from chino to jersey shorts. Just try to go for a neutral colourway if you want to get the most wear out of them. Black, grey and white will go with everything. Neon green on the other hand, not so much.

Loafers

Driving Shoes Deco Calf Leather, £320 at CAR SHOE >
Tod’s Penny Loafers, £320 at HARRODS >

The question that has puzzled men for decades is what to wear in place of a smart shoe when trousers have been replaced with shorts. Have you ever tried wearing a Derby with no-show socks and your legs on display? Suffice to say, it’s not a great look. Instead, opt for a pair of loafers, which are ideal for creating smart casual outfits when combined with tailored or chino shorts and a crisp shirt.

Boat (Deck) Shoes

Sperry Authentic Original Burnished-Leather Boat Shoes, £85 at MR PORTER >
Sebago Docksides White Washed Grises, from £85.06 at AMAZON >

Boat (or deck) shoes were invented by Paul Sperry in the 1930s – quite literally for the purpose of remaining sure-footed on the deck of a boat – and have gone on to become a mainstay of summer preppy style. As such, they look superb teamed with a pair of chino shorts and a button-down Oxford shirt.

Shorts And Shoes Combinations For Every Summer Occasion

Beach To Bar

Onia Charles Swim Shorts, £106 at MATCHESFASHION >
Birkenstock Milano Birko-Flor, £60 at BIRKENSTOCK >

Dressing on holiday can be tricky. When you’re used to dealing with rain and clouds the vast majority of the time, being thrust back into the sun can be daunting. However, the rise in popularity of tailored swim shorts have made things a whole lot easier. Brands like Orlebar Brown, Onia and Frescobol Carioca are producing shorts that look equally at home in the pool or out for a spot of al fresco dining.

To get the look right, team tailored swim shorts with a pair of strapped, leather sandals. Then simply throw on a polo or Cuban collar shirt and you’re good to go for beach, bar and everywhere in between.

Poolside

Vilebrequin Moorise Ancient Turtle Swim Shorts, £185 at HARRODS >
Adidas Adilette Slides, £30 at MR PORTER >

As far as outfit choices go, what to wear around the pool is about as self-explanatory as it gets. But there are still a few things you should bear in mind. First of all, the length of your shorts is key – don’t go too short nor too long. Instead, try to strike a balance somewhere in the middle. A good rule of thumb is that your shorts should end a couple of inches above the top of the knee.

Footwear wise, you’ll want something you can slip on and off with relative ease. That means lace-up shoes are out and sliders and sandals are in. Just don’t wear them with socks, regardless of what current fashion trends may be telling you.

Athleisure

French Terry Tracksuit Shorts, £25 at ARKET >
Nike Blazer Low Trainers, £70 at ARKET >

Athleisure was one of the hottest trends in menswear for several years, but rather than fading away into obscurity it has simply become the new normal. And that’s no bad thing, because not only is this style of dress supremely comfortable, but it looks great too.

Opt for jersey shorts in black or grey that finish just above the knee. Then throw on a plain white T-shirt or polo and style with a pair of smart, white leather sneakers.

Summer In The City

Standard Chino Shorts, £45 at ARKET >
Converse Jack Purcell Signature Canvas Sneakers, £80 at MR PORTER >

Shorts in the city has always been a hotly-debated topic. Some menswear mavens will tell you that to brave town in anything but full-length legwear is a cardinal men’s style sin. But we say ignore the naysayers – getting it right is simply a matter of selecting the right tools for the job.

For a fail-safe, everyday ensemble, combine chino shorts with canvas trainers – either a lace-up, like Converse, or a slip-on, like Vans – and wear with a short-sleeved shirt. Simple.

Evening Out

Navy Linen And Cotton Shorts, £79 at SUITSUPPLY >
Harvard II Dark Brown Suede Loafers, £345 at CROCKETT AND JONES >

The prospect of adhering to a smart casual dress code when it’s 30 degrees in the shade is admittedly rather unappealing. Yet it doesn’t have to be. With a pair of tailored shorts you can be smart and comfortable all at once.

The key to pulling it off is to find the right shoes – and loafers are about as safe a bet as it gets. Wear a brown suede pair with no-show socks and team them with a printed, short-sleeved, Cuban-collar shirt on top.