5 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 for every man. But when do you chose denim and when do you go for a chino cut? We’ve got a full briefing on what ones to go for and what shoes to wear with your 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, the beer gardens begin to fill out and the nights get longer, you know it’s time you got your legs out and whack on a pair of shorts. But, knowing exactly what shoes to wear with your shorts can cause quite a few headaches for some. Are they too chunky? Do they look smart enough? Are sandals acceptable? Do you dare to wear socks? The questions are endless. So if any of these are mulling around in your mind, we’ve got a few short and shoe combinations for you to try out. And the best thing is, if you’re ever stuck again, we’ve got five ways for you to wear your shoes and shorts without making any major style mistakes.

The Fit of the Shorts

When it comes to the fit of your shorts you have two main options to go for – just above the knee or halfway 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 three quarter lengths look good at the moment. If you’re a taller guy with long legs, it’s probably best to 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, plus the shorter the short the longer your legs can look.

mens summer street style blue t-shirt denim shorts trainers
Summer Shorts


Men’s Jersey Casual Shorts

So it’s now time to figure out what shorts go with what shoes. Jersey shorts are by far the most casual style we’re going to be looking at here. These shorts are perfect for the gym, lazing around the house or even a summer’s afternoon of barbecuing with your mates. But what you need to remember about jersey shorts is that they are casual and you shouldn’t be trying to mix this into your smart-casual wardrobe. You need to keep the jersey fabric relaxed and pair them with an equally as relaxed pair of 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 knowing you need to be casual but how casual is casual? For a comfortable and laid-back look, go for some canvas plimsolls. And if you’re heading off for a workout or you just want a street aesthetic, you’re gonna need some trainers. Your trainers will be a big factor in your outfit so choose them wisely. And finally, if you’re in much hotter climates, you can always try a pair of flip-flops or sandals. A walk along the beach shouldn’t really involve trainers because sand and socks aren’t the best combinations out there.

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

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 a good pair of tailored shorts for men. A perfect alternative to the smart trousers, you could even match them with a navy blazer, white shirt and some slimline loafers.

Chino shorts can look both smart and casual

Men’s Denim Shorts

We’re great believers in never saying never, so we feel there’s always room to smarten up some denim shorts however casual them may appear to be. Denim shorts offer a bit more durability than the other styles we have mentioned, and are versatile enough to pair with almost any casual or smart-casual outfit. You can smarten them up with a polo shirt or, at a stretch, an Oxford shirt, but, in general, we’d stick to T-shirts, checked shirts and sweats. This keeps the general casual feel of the denim in tact and doesn’t make the look seem lilke you’re trying to make it too smart.

When it comes to shoes that’ll go with denim, 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 running trainers either. You can also pair these with sandals or flip-flops if you’re on holiday and the temperatures are high, but when it’s really hot, you may want to switch up the denim for a thinner, looser style.

Men’s Tailored Shorts

Tailored shorts are probably the least commonly-owned pair of shorts on this list but a viable option nonetheless. These are obviously ideal for those of you that need to smarten up at work but can’t get away with the chino short option. These shorts mainly need to be paired with smart shoes like loafers or brogues as you are most likely going to wear them to formal occasions. This doesn’t mean you have to always pair them with other pieces of smart tailoring, as a simple shirt will do, but you do need to keep your footwear tamed.

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 toes, then either boat shoes or leather sandals will also do the trick. Slightly less formal but still able to work well.

shorts white shirt
Your shorts can go with an array of shoe styles

Men’s Swim Shorts

Now, we know you’re not usually looking to spruce up your swimwear with a pair of shoes 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. 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 sliders. 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. There’s so many light options to go for so you’re not simple restricted to just flip flops.

What Shoes to Wear With Shorts

  • Casual shoes and trainers – are a perfect match for jersey shorts to create a casual, laid-back and relaxed 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. White trainers are always the safest if you’re unsure.
  • 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. The main thing to think about is the context, where are you wearing these shorts and are your shoes attire appropriate?


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Shorts are a Summer must-have for every man. But when do you chose denim and when do you go for a chino cut? We’ve...
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