The Right Shoes To Wear With Every Type Of Shorts

Failsafe bottom-half combos to get you through summer 2022 in style.

Wearing a pair of shorts isn’t exactly brain surgery, but combining them with the right shoes can be. Given that shorts don’t have a bottom half, they show off far more of your shoes than trousers ever can, meaning picking the right pair can make or break a look.

Sneakers might be the default option but go too sporty with smart casual pieces and the outfit won’t work. Likewise, break out your leather deck shoes or loafers with the wrong shorts and it will just look wrong.

So from matching sandals with chino shorts to white kicks with swim shorts, below you’ll find a number of failsafe bottom-half combos to get you through summer in style.

What shoes to wear with chino shorts

Arguably the most versatile of all shorts styles, chinos are the smart casual short, the one that works as well with an Oxford shirt as it does a throw-on tee. Wear these to the pub on the weekend, for lounging around the house on a warm day or even to the office if your workplace doesn’t have an anti-calves policy. As for the shoes that go with them, the options are vast, but there are a few styles that work best.

Canvas low tops

Men's navy shorts with white Cuban collar shirt and sneakers outfit

ISTO

A natural pairing for chino shorts, canvas low tops are timeless, comfortable and adaptable. Despite their history as one of the first basketball shoes in existence, this classic silhouette has transcended its sporty roots to become an all-time, all star among the myriad wardrobe staples that dominate menswear today.

Usually available in navy, black or white, this is a style that perfectly combines with stone chinos, and works as well without socks as they do with. They undoubtedly add a casual edge to chino shorts as opposed to leather shoes which would smarten them up, but their versatility and classic design will see you reach for them more often than not.

Leather sandals

Men's chinos shorts, floral shirt and leather sandals summer outfit

Mango

Sandals scream summer. There’s few better feelings than slipping into a pair and leaving the house in the heat, but choosing the right style makes all the difference. Classic leather sandals have been worn for thousands of years, and were some of the first shoes in existence, taking the word ‘timeless’ to new depths.

The best sandals today aren’t all that different from pairs the Romans and Ancient Greeks wore back in the day. A simple leather or rubber footbed is moulded to a leather, strappy upper, allowing your feet to slide in unhindered. Depending on the style, you could go for a simple, two strap set up, which is arguably the most comfortable, or something more intricate like a woven leather fisherman-style sandal.

Either way, a brown pair is the perfect accompaniment to chino shorts and a T-shirt in summer, while they can also double up as a house shoe in winter when worn with socks.

Retro running shoes

Men's shorts, henley top and canvas sneakers outfit

Rag & Bone

Retro runners have enjoyed something of a renaissance over the past few years. Seemingly coming from nowhere, brands began scouring through their archives, turning to their designs of the 70s and 80s for inspiration. The era was arguably the best for running shoe design, spawning plenty of classic models that look as good now as they did then.

From simple, suede panelled designs through to more high-tech mesh uppers, retro running shoes are ideal for pairing with smart casual pieces like chino shorts. Plus, they often come available in a range of colourways, meaning you can easily jazz up your look with a flash of red, blue, green or yellow down below.

Don’t forget to pair them with equally retro white or grey sports socks, either plain or with stripes, for added style kudos.

What shoes to wear with tailored shorts

These are shorts in their smartest form. Essentially a pair of suit trousers cut in half, tailored shorts are what you wear when you need to be as smart as possible in the warmest of conditions.

Often crafted from fabrics like cotton twill, wool and linen blends, tailored shorts combine well with shirts and knitwear but can also dress up the humble tee. When it comes to the shoes you wear with them, it’s worth sticking to the smarter end of the spectrum, although luxe minimal sneakers are also welcome.

Loafers

Men's smart casual shorts, shirt and loafers outfit

Ralph Lauren

Loafers are an underrated summer shoe. Often shunned in favour of derbies, loafers are smooth, comfortable and evoke a lost era of mid century elegance. But you’ve got to pick the right ones. Loafers can be dreadful, and all too often mimic the ‘going out shoes’ your uncle would wear to the club in the 90s.

When it comes to pairing them with shorts, there’s really only one style worth checking out: the penny loafer. With its heritage as a Norwegian fishing shoe and later as a preppy icon widely adopted by 60s Ivy League types, penny loafers are classic. They’re smart but not stuffy, comfortable and mostly very well made. And they go perfectly with tailored shorts.

Look for a pair made from waxed, dark brown leather and with the style’s signature ‘beef roll’ stitching on either side of the vamp. Wear them with hidden socks and you’re good to go.

Leather deck shoes

Men's tailored shorts worn with knitted polo shirt and unstructured blazer outfit

Boglioli

Another seasonally-appropriate option, a leather deck shoe is about as smart as you’d want to go with shorts; anything sharper, like oxfords and most derbies, would look too severe, firmly placing you into public school boy territory.

Deck shoes on the other hand were born to be worn with shorts. When it comes to matching them with tailored versions, swerve multicoloured designs and stick to navy or brown leather for ultimate versatility.

Wear them with knitted polos, Cuban collar shirts and soft, unstructured tailoring to channel that traditional Italian elegance.

Suede sneakers

Men's tailored shorts with blazer, polo shirt and suede sneakers outfit

Brunello Cucinelli

As far as versatility goes, your best option with tailored shorts might just be suede sneakers. An underrated material for sneakers, suede adds a luxe element that not even the finest leather can rival. Find the right pair of suede kicks, combine them with tailored shorts and you’ll be perfectly tracing the smart casual divide.

What should you look out for? The style of sneaker should be your main consideration. Look to minimal designs based on classic tennis shoes and you’ll be in the right place. With simple, panelled uppers and clean, tonal soles, suede minimal shoes are an ideal match to navy tailored shorts. Or you could go with something a bit more interesting with a suede pair of retro runners.

Keep the colour palette tonal, either matching the shorts or providing a subtle contrast, or go for something bright and bold to stand out among an otherwise pared-back look. The choice is yours.

What shoes to wear with swim shorts

You’d be forgiven for thinking swim shorts were only worn by the beach or the pool. But, increasingly, brands are producing them in simple, quick-drying designs that look just as good away from the water as they do in it.

That means you’ll often be required to wear shoes with them from time to time. Of course, swim shorts are a natural partner for flip flops/sliders, but you might have to up your game if you plan to go from pool to the bar in style.

Espadrilles

Men's swim shorts with linen shirt and espadrilles vacation outfit

The Resort Co

Espadrilles are an underrated summer footwear option, often shunned in favour of flip flops and sandals. The classic canvas design, which dates back centuries, ensures they’re a stylish option for pairing with swim shorts, regardless of whether you’re on the beach or not.

Originating in the Catalan region of Spain, espadrilles weren’t intended for style; rather, they were a cheap, easy to make footwear option for people who couldn’t afford leather shoes. Often worn by fishermen or peasants from the 14th century onwards, espadrilles served a purpose.

Today they’ve well and truly shed their humble roots, and while they still boast a rustic charm they’ve become a durable alternative to leather sandals and flip flops. Look for a pair in traditional, undyed canvas and with a classic esparto rope sole, which is incredibly strong and built to take a beating.

Flip flops and sliders

Men's swim shorts worn with pool sliders outfit

Marks & Spencer

We wouldn’t usually advocate the wearing of flip flops. But what they lack in dignity they make up for in practicality. At least when you’re sat beside the pool. Indeed, wear flip flops anywhere other than the pool or beach and your outfit will likely be instantly tarnished.

As long as you’re in the vicinity of water, however, all is well, especially when coupled up with swim shorts. When looking for your own pair, try to keep things as simple as possible – think simple black flip flops that know their place and lack any novelty branding or anything that draws unnecessary attention to them.

There’s a little more room for styling with sliders. You’ll find them in colours, gentle patterns and emblazoned with bold branding. It’s a love-hate look but works well for throwback swimwear fits.

White sneakers

Men's swim shorts, linen shirt and white sneakers outfit

H&M

White sneakers rarely disappoint. The most versatile of sneaker styles, minimal white kicks can be worn with virtually anything, from jeans and a tee to an unstructured suit. They’re also a great companion to swim shorts, especially if you intend to wear them away from the beach.

Find a pair of tailored swim shorts in a simple, plain colour or pattern and you can wear them throughout the day on vacation, confident in the knowledge you can jump into the nearest body of water any time you please. Plus, when you’re out and about, trusty white kicks will stay comfortable in a way that espadrilles or sandals sadly won’t. A simple solution and one that slightly dresses up the swim short with low-key style.

What shoes to wear with jersey shorts

Cotton jersey shorts might be the most underrated style on our list. Essentially a shorter version of your classic sweatpants, they’re comfortable, easy to style and work as an excellent alternative to the smarter chino and tailored variety.

Perfect for a streetwear-inspired summer look, athletic shorts boast an elasticated waist and a slightly stretchy jersey fabric, making them virtually as comfortable as pyjamas. Ideal for wearing on weekends with hoodies, tees and sweatshirts, they’re relaxed and laid back, and require a shoe that matches their casual nature.

Knitted sneakers

Men's jersey shorts, cardigan and knitted sneaker soutfit

Brunello Cucinelli

For unrivalled comfort, knitted sneakers are the way to go. Often constructed with a soft, knitted upper which feels like a reinforced sock against the foot, these are shoes you can wear day in, day out without trouble. Often coming in running or training shoe silhouettes, knitted sneakers have a sporty feel that perfectly complements jersey shorts, in both look and feel.

This is a no-going-back combination; everything else feels uncomfortable and restrictive by comparison. While you could introduce colour via your footwear, an easy way to pull off the combo is by going tonal. Try a pair of black jersey shorts with matching black knitted trainers and finish with a crisp white tee for a simple weekend look that will never fail.

Trail runners

Men's jersey shorts worn with trail running shoes

Castore

Trail runners have been in the spotlight for some time. Think technical designs with jagged, grippy rubber soles and panelled, colourful uppers designed to conform to the foot for hilly running sessions in the countryside. These futuristic-looking shoes are often genuine performers, but if you’re after a high-tech aesthetic then they’re also perfect for wearing casually with similarly sporty pieces like jersey shorts.

You can go tonal like the above, but this style is also a good opportunity to add some colour, with bright blues, yellows and oranges often working well against the muted grey or black of the shorts.

Minimal sneakers

Men's jersey shorts, white t-shirt and white sneakers outfit

Closed

For understated cool, you can’t go wrong with minimal sneakers. Available in a spectrum of subtly different styles, this is a shoe that will work just as well now as it will in five years’ time, providing you invest in a quality pair and maintain them regularly.

Look for a pair in grey suede or nubuck, and combine them with classic grey marl jersey shorts for a timeless pairing and one that works with simple tees, polos or hoodies.