What to wear with shorts

24th May 2018

Sun’s out – shorts out.  Now that summer’s arrived you’re probably wondering if it’s time to tuck the jeans aside and embrace shorts. 

Whether you’ve got BBQs lined up every weekend or are grabbing your passport for a wild week with your mates – you’re gonna need to nail this look.

When can you wear shorts?

Shorts work for day or night and can be both smart or casual. Wear smarter styles – such as chinos – to a summer wedding, a night out or a date at the weekend.

They’re also the perfect choice if you’re travelling this summer, heading to a festival or just chilling with mates in your down time.

Basically, when the sun comes out – the shorts go on.

How should shorts fit?

Shorts should always be comfortable – try to avoid anything too tight or you’ll be struggling to sit down or use the pockets. Choose a cut that sits looser on the leg – while a good fit around the waist ensures they don’t look shapeless.

shoes to wear with shorts

What shoes to wear with shorts

Pairing shoes with shorts can feel like the toughest task – there’s a lot more bare leg to consider and you want a look that’s flattering. Here, we’ve broken it down.

What shoes go with chino shorts?

These are a smarter choice, so your shoes need to match. Loafers or brogues are the best call. Go for tan or brown.

What shoes to wear with cargo shorts

Stick with retro style sneakers when you’re pairing up shoes with cargo shorts – smaller, low-rise shoes are the best choice. We’re also all about colour clashing, so choose a white trainer with an unexpected primary stripe to really up your fashion game.

What shoes to pair with denim shorts

With these faithful heroes, you can pretty much get away with any shoe but trainers are always a good call for day-to-day wear. If it’s warm, stick to sliders – unless you’re at a festival. A cross body bag finishes off any look, giving you easy access to everything while rocking that 90s style at the same time.

Shoes that work with board shorts

Swimwear definitely works with sliders. It’s the ideal choice for chilling poolside in the day. Grab a short sleeved shirt, spruce up your hair and you’re good to go for bar hopping in the evening. Swap out your sliders for trainers and add sports socks for a lowkey athleisure vibe – once you’re done by the pool.

shirt to wear with shorts

What shirt to wear with shorts

These are the best shirts to pair with your shorts:

  • Long sleeved shirt – Ideal for laid back days that turn into wild evenings.
  • Short sleeved shirt – Look for a strong print for your holidays.
  • Polo shirt – Great for everyday styling.
  • Plain t-shirt – The best choice for that throw on and go vibe.
  • Shirt – A strong collar and a button up style makes an impression when paired with fitted chino shorts.

Dos and don’ts when wearing shorts

Do look for shorts with plenty of pockets – Leave the baggage at home.

Do think about fabric – Bear in mind that on particularly hot days, a thicker material might not be your best friend – so that means losing the cargos for chinos or board shorts. Remember to check the forecast.

Do grab one in every colour – A grey, navy or tan pair of shorts will see you through all summer and can be mixed and matched with all the shirts in your wardrobe – but don’t be afraid to dabble in colour too. A strong, patterned short looks great with a plain shirt or you could go for a bold red or green to stand out from your mates.  

Don’t wear chunky shoes – Anything too high or chunky – such as boots – puts emphasis where you don’t want it. Stick to slip on styles that look great and finish off your outfit instead of dominating it.

Don’t be afraid to wear them for smarter occasions – Tailored shorts look great with a shirt and a blazer for a more casual summer wedding or a party happening in town.

outfit ideas for shorts

Outfit ideas for shorts

Still looking for inspo? Here are some ideas on what to wear with shorts –

Long sleeved t-shirt + denim + sliders

A long sleeved t-shirt is the ideal choice for evenings out with mates. Pair with denim or chino shorts and finish off with sliders. Add a lightweight bomber jacket if the summer weather has taken a turn for the worst.

Short sleeved shirt + chinos + sliders

Ideal for exploring the strip on your holiday, pair a short sleeved shirt in a strong print with chino shorts in a bold colour. Our Miami Loom Shirt comes to mind, with a Hawaiian inspired print – wear with a few of the top buttons undone to show off that new tan.

Clashing prints + sports socks + trainers

Don’t be afraid to clash prints when pulling together a look. Camo print cargo shorts and a graphic print tee might not sound like the perfect partners but throw them on with sports socks and a bold trainer and you’ll be turning heads for all the right reasons.

Plain t-shirt + cargo shorts + bomber jacket + trainers

A v-neck, plain t-shirt always looks good, in a basic colour such as black, white or grey. Pair with your cargo shorts or denim style – ideal for laid back days. Throw on a bomber jacket for the evening.

Shirt + chino shorts + blazer + espadrilles

Look for a dress shirt featuring a print to wear with chino shorts. Pair a striped shirt with red chino shorts or wear a white shirt with dark coloured shorts for a sophisticated vibe wherever you end up. Ideal for a summer wedding or the hotel cocktail bar. Finish the look with espadrilles. Add a blazer for photos.

Men’s shorts 2018

These are the on-trend styles for the summer ahead.


This year, cargo shorts are no longer reserved for your Dad. They’re the ultimate festival choice, with pockets that rival any bum bag. Look for heavier material that can take everything you throw at it, in a navy or khaki shade.


Ideal for those dressier summer events, chino shorts look great with a polo shirt and slip on loafers. Choose these for that wedding you’re attending in the evening, if it’s really warm, or if you’re heading into town on a Saturday.


These shorts are going everywhere with you this summer. Frayed or turned up denim is in right now and looks great whether you’re hanging down the beach for the day, heading to the airport or just chilling at the weekend.

Board shorts

Stick with us here, board shorts now look good enough to leave the house in – don’t just reserve them for the pool. A strong graphic works with a plain t-shirt and sliders, for a chill everyday look.

Ditch the jeans and embrace the shorts this summer. Try out these looks and tag us in your Insta snaps using the hashtag #mysuperdry.

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