Cut-Off Conundrum: How To Pick The Right Shoes To Match With Shorts

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, here we run through some key shorts styles and detail the perfect footwear options to pair with each one.

The Best Shoes For Athletic Shorts

Whether you’re hitting the gym or doing the exact opposite and enjoying a Sunday-afternoon Netflix binge, a pair of comfortable athletic shorts is the perfect partner. Look to sportswear brands like Castore, Reigning Champ and Nike for stylish options.

Retro Runners

When they’re not looking to the future, many sneaker brands like to draw on the archives for inspiration. The resulting throwback styles make an ideal match for athletic shorts. Check out brands like Spalwart, Nike and Saucony – all of which are solid choices when it comes to your retro, suede track-shoe needs.

Minimalist Sneakers

Bulky, “ugly” sneakers may be having a moment, but that doesn’t mean minimalism is redundant. Much more than a trend, styles like the Axel Arigato Clean 90 and Adidas Stan Smith are timeless classics that you can keep marching out year after year. Keep things simple in plain white leather, or team a pastel pair with some grey jersey shorts to add a subtle splash of colour.

Knitted Trainers

Athletic shorts call for athletic shoes. Knitted trainers are comfortable, practical and just so happen to look pretty slick, too. The definition of athleisure. Adidas’ Ultra Boost and Nike’s Epic React are good everyday choices, while the likes of Balenciaga and Maison Margiela offer up some more runway-friendly options.

The Best Shoes For Chino Shorts

In terms of day-to-day wear during the summer months, it doesn’t get much better than a pair of chino shorts. This warm-weather wardrobe staple boasts unrivalled versatility and can be easily dressed up or down depending on the occasion.

Canvas Sneakers

Canvas plimsolls like the Converse Chuck Taylor All Star are a strong contender for World’s Favourite Type Of Shoe. And one of the many things they pair with perfectly is chino shorts. Keep things classic with a low-top version like Converse’s All Star Ox 70 or Novesta’s Star Master in a neutral, earthy or even a pastel shade.

Boat Shoes

You don’t have to be strolling around the deck of a superyacht in order to pull off boat shoes. Simply team a brown leather pair with a crisp white polo shirt, tucked into slim-fit, beige chino shorts for a fail-safe smart-casual summer look.

Leather Sandals

Flip-flops are great, but there’s a time and a place for them (i.e. the beach). Anywhere else, a pair of leather sandals from a trusted label like Birkenstock offers a stylish compromise. They’re appropriate for the beach but stylish enough to be worn out for an evening meal while abroad when paired with chino shorts and a refined Cuban-collar shirt.

The Best Shoes For Tailored Shorts

At their core, shorts are casualwear. This is something that leads many men to believe they can’t be dressed up. However, thanks to the merging of dress codes in almost all areas of menswear, it’s now possible to don a pair and still look put together.


Teaming shorts with Derby shoes may seem like a good way to end up looking like a schoolboy from the 1940s, but it can be pulled off. Tailored shorts make this seemingly unusual summer footwear choice a viable option. Go leather for classic, or suede for something more relaxed and in tune with the season.


As far as smart-casual footwear that looks good with shorts goes, it doesn’t get better than loafers. These timeless slip-ons can be combined with tailored shorts for any occasion that requires a bit of refinement – think summer garden parties, evening drinks and beyond.

Luxe Sneakers

You likely wouldn’t think to put tailored shorts and sneakers together. Yet going premium in the footwear department allows you to dress down your legwear without appearing sloppy. Stick to clean, leather styles from the likes of Common Projects, ETQ. or Buttero. To bring the look together, throw on a pale-blue Oxford shirt and top it off with your favourite sunglasses.

The Best Shoes For Swimming Shorts

Don’t fall into the trap of thinking swimming shorts are just for, well, swimming. Pick the right pair and wear them with the right footwear and there’s no reason you can’t stride directly from beach to bar. Shop simple block colours to keep it classy or go for something bold and vibrant to make a statement.

Flip Flops

When lounging around by the sea or the pool, flip-flops are the only footwear that will cut it. Thankfully, they happen to look rather good with swimming shorts. Just stick to plain designs in hues that complement your skin tone and it’s impossible to go wrong. Black or grey flip-flops with pastel shorts will always be a strong choice.


If sandals and flip-flops simply aren’t your thing, that’s fine – there’s another beach-friendly option that works just as well with swimming shorts. Espadrilles are the often-unsung hero of the resortwear world. They’re comfortable, casual and easy to take on and off when you’re flitting between the sand and the streets.

Canvas Sneakers

Pair plain black or white canvas sneakers with some statement swimming shorts for an impactful holiday look. The shorts can do the talking while the simplicity of the sneakers keeps things grounded.

Go-To Shorts & Shoes Combinations For Every Summer Occasion

Beach To Bar

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.


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 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

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

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.

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