14 Perfect Shorts & Shoes Combinations

what shoes to wear with shorts mens street style
PHOTO CREDIT: All That I Covet

Shorts are a Summer must-have! Get a full briefing on what shoes to wear with men’s casual shorts and men’s smart shorts in this comprehensive guide that covers all styles and shows you how to wear them properly.

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When the sun starts to shine and the beer gardens begin to fill and the nights get longer, you know it’s time you got your knees out and whacked on some shorts. Knowing exactly what shoes to wear with shorts can cause quite a few headaches for some. Are they too chunky? Do they look smart enough? Are sandals acceptable?

These are just a few questions you may be mulling over in your mind when pairing your shorts and shoes together. So, to make sure you never have those worries again, we’re going to be looking at the various shorts styles you’ve got to choose from and the footwear that best suits them.

The Fit

When it comes to the fit of your shorts you have two main options – just above the knee or half way up your thigh. You don’t want them falling on your knee and you certainly don’t want them halfway down your shin – it’s not the 90s and no one’s making that look good at the moment. If you’re a taller guy with long legs I’d probably go for a length that sits just above your knee. Shorter legs can get away with them finishing halfway up the thigh for an 80’s aesthetic.

what shoes to wear with shorts
Two men wearing shorts and shirts
PHOTO CREDIT: Pinterest

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Men’s Jersey & Casual Shorts

Jersey shorts are by far the most casual style we’re going to be looking at here. These shorts are perfect for the gym, lazy days around the house or even a summer’s afternoon of barbequing with your mates. But, as ever in this current climate of mixing the smart with the casual, you shouldn’t be afraid of pairing them with some slightly more formal pieces for a contemporary finish that’ll take you from the beach to the bar with ease.

what shoes to wear with shorts
Two men wearing shorts
PHOTO CREDIT: Pinterest

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The Shoes

When it comes to pairing up your shoes with some jersey shorts, you need to be thinking about context. It’s all well and good blending smart and casual together but if you’re heading to the gym, you don’t wanna be rocking a pair or derbies, do you?

For a comfortable and laid back look, go for some canvas plimsolls. If you’re heading to a workout or you want a street aesthetic, you’re gonna need some runners. If you do want to try smartening them up, why not go for some suede penny loafers? Or, if you’re in much hotter climates, you can always try a pair of flip flops or sandals.

Adam Gallagher wears shorts and boat shoes
Adam Gallagher teams chino shorts with boat shoes
PHOTO CREDIT: IAMGALLA

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Styling Them Together

Jersey shorts may look very casual, but they’re fairly easy to smarten up. Take a plain white oxford shirt and wear them both with a pair of club master sunglasses. Chuck on a pair of canvas plimsolls or plain tennis shoes to finish the look.

A man wears a vest with shorts and converse
A man pairs chino shorts with vest and Converse trainers
PHOTO CREDIT: Pinterest

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Men’s Smart & Chino Shorts

Chinos strike that happy medium between smart and casual, making them super easy to dress up or down. Perfect for office wear, if your place of work allows it, they are also ideal for pairing with smarter shoes.

You don’t have to stay smart with them, though. You can add more casual trainers to the look, but we’d resist the temptation to pair them with overly street pieces. These also come in a range of colours so it’s worth getting men’s smart shorts in light and dark pairs, just for versatility in your wardrobe. You could even opt for a print, such as stripes if you wanted a slightly more individual finish.

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Team your chino shorts with a shirt and boat shoes
PHOTO CREDIT: Pinterest

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The Shoes

When it comes to choosing what shoes you’re going to wear, there are a few styles that will give you a great smart finish. For a proper summer vibe and what to wear with white shorts, go for some boat shoes and finish the nautical look off with a Breton stripe T-shirt and some Wayfarer Sunglasses.

If you’re off out for dinner, make sure you opt for tailored shorts for men. A perfect alternative to the smart trousers, you could even match them with a navy blazer, a white shirt and some slim line loafers or desert boots. Finally, you could even go for some running trainers or plimsolls, the footwear world really is your oyster here.

Oliver Cheshire shorts and t shirt
Oliver Cheshire wears shorts and trainers in London
PHOTO CREDIT: Pinterest

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Styling Them Together

Pair your chino shorts with a navy blazer, white shirt and some boat shoes or loafers. This will create a classically cool smart-casual look that sticks to the basics. This look is perfect for formal events in the summer.

man in chino shorts and loafers
A man wears chino shorts with loafers
PHOTO CREDIT: Pinterest

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Denim

We’re great believers in never saying never, so we feel there’s always room to smarten up some denim shorts. Denim shorts offer a bit more durability than the other styles we have mentioned, and are versatile enough for pairing with almost any casual or smart-casual pieces. You can smarten them up a touch with a polo shirt or, at a stretch, an Oxford shirt, but, in general, we’d stick to T-shirts, checked shirts and sweats.

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PHOTO CREDIT: Lookastic

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The Shoes

When it comes to shoes, the casual footwear world is at your full disposal. Everything from high-top Chuck Taylors to Vans Classics are going to suit these. If you’re after a sportier aesthetic, don’t be afraid to team them up with your runners either. Obviously, you could pair these with sandals/ flip-flops if you’re on holiday and the temperatures are high, but the two looks are fairly conflicting. You really want to stick to a rugged finish.

Johannes Huebl and Olivia Palermo in shorts
Johannes Huebl and Olivia Palermo
PHOTO CREDIT: Pinterest 

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Styling Them Together

Opt for a green checked shirt (layer over a plain white or black tee if you want), some lighter blue denim, Vans or Converse Chuck Taylors and finish off with a bit of attitude for a grunge look.

Tailored

These are probably the least commonly-owned pair of shorts in this list but a viable option nonetheless. There are obviously ideal for people who need to smarten up at work (but can’t get away with the Chino option) or, if you’re really lucky, people heading to a wedding in the Bahamas.

You don’t have to be pairing them with other pieces of tailoring, though, and you can dress them down a little so they better suit a weekend with a printed shirt or knitwear.

what shoes to wear with shorts
A man wearing a shirt and blazer
PHOTO CREDIT: Aida Shoreditch

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The Shoes

The footwear you pair with these decidedly formal shorts should be kept presentable and shouldn’t be part of your weekend wardrobe rotation. Try some streamlined loafers or drivers or even some suede derby shoes. If you’re in dire need of some air for your hooves, only stick to leather sandals – no flip-flops or slides!

Adam Gallagher wears shorts and boat shoes
Adam Gallagher Wears Boat Shoes
PHOTO CREDIT: IAMGALLA 

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Styling Them Together

For a summer’s evening, team your tailored shorts with a decent bit of knitwear, an Oxford shirt and some penny loafers to finish it off. For an added season-appropriate extra, try a pair of Clubmaster sunglasses.

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Swim

Now I know you’re not usually looking to spruce up your swimwear but sometimes you need to head to the bar for an ice cold beverage or a snack so it’s worth taking a look at what pieces will dress them up slightly. For this, stick to simple tees, short sleeved shirts (maybe with a print if your swimmers are fairly plain) or your vest. The footwear kind of depends on context.

mens swim shorts
Three men wear patterned swimming trunks
PHOTO CREDIT: H&M

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The Shoes

If you’re chilling by the pool or beach, you’ll want to opt for your flip-flops, sandals (if you think they’re an acceptable choice of footwear, we’re still undecided) or slides. If you’re going to be walking across uneven ground and need something a little more supportive, go for canvas plimsolls or streamlined tennis shoes.

Styling Them Together

Let’s keep things simple here and go for the short sleeved shirt, swim shorts and flip flops, quite smart (to impress that girl you’ve been eyeing from across the beach) but still practical and breezy enough to avoid sweaty feet ensuing!

Men Wearing Shorts

The best place to find some inspiration when you’re wearing shorts is the street. There, you’ll be able to see what styles you like the look of and what you think will incorporate well into your wardrobe.

adam gallagher green shorts white shirt mens street style
Adam Gallagher wears a shirt and boat shoes
PHOTO CREDIT: IAMGALLA

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What Shoes to Wear With Shorts

  • Casual shoes and trainers – a perfect match for jersey shorts for a casual look.
  • Loafers and brogues – formal shoes work great with tailored chino shorts – just remember to ditch the socks and grab a pair of sunglasses.
  • Trainers – the best option for denim shorts to keep in with the casualness of the outfit.
  • Sandals and flip flops – these should only really be worn with swimming shorts.
what shoes to wear with shorts
A Jumper With Loafers
PHOTO CREDIT: G.H. Bass and Co.

On That Note

Matching your shorts with shoes doesn’t have to be hard. As long as you follow this guide, you should be able to pick out the best shoes to match your outfit. Don’t overthink it, and if in doubt just opt for a minimal and clean pair of white trainers which will suit most styles. Head over to our website to check out our shorts and shoes to make sure you have all outfits covered this summer.

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