How to Wear Shorts This Season

How to Wear Shorts This Season
PHOTO CREDIT: Aida Shoreditch

Here at Idle HQ, we’re on a bit of a mission. It’s a humble one but we think it’s very important. We want more men (ideally ALL men) to start wearing shorts.

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It’s now officially barbeque season, beer garden season, holiday season and taking-your-speakers-to-the-park-for-a-jam season. That means it is shorts season too, and every guy we see sweating his face off in jeans on a hot, sunny day…well. That’s a missed opportunity. Just think of all the weather-appropriate clothing options the dude could have gone with. But he just couldn’t do it.

We see you and we hear you, shorts sceptics. We understand it can be hard to find shorts that look good – and hard to know what’s okay to wear with them once you’ve found them. Fear not, we’ve put together a pretty comprehensive guide to the right shorts for different occasions and some styling notes to help you nail the whole look. Read on, embrace your legs and join us to wear shorts coolly and confidently all together, all summer.

Oli Wood / Lookbook
Pair shorts with box-fresh white trainers


The Basics

  • You have three main options with the length. Styles that are cut just above the knee are flattering and current. Many of our casual shorts stop above the knee, and if you’re going smart then this cut is the only way to go.
  • If you go for long shorts you’ll have a choice of sporty designs and laid-back jersey shorts. Both can look pretty sick and, it has to be said, both are outrageously comfy for the days when leaving the house just doesn’t happen.
  • There are some brave men who will back themselves enough to go retro with shorter shorts. There aren’t as many of these styles about, but if you find some that you like then we say go for it – be bold. Your tan will thank you.
  • Length aside there are virtually no other limitations on where your fine taste in shorts could take you. You can find shorts in every fabric – if there are trousers made from it then there are shorts made from it too. Experiment with prints, colours and logos too – otherwise you’ll never fulfil your true shorts-wearing potential.
mens Shorts street style
Three ways to style shorts


The Rules

Well, we say rules. In reality, it’s not really for us to say what you should and shouldn’t wear, just to make suggestions and offer friendly advice. Here are three rock solid pieces of shorts-wearing best practice that apply across the board, whatever the outfit and whatever the occasion.

Only Wear Shorts When it’s Hot

We really are starting with the rudiments here. If it’s cold and you’re in shorts, not only will you be freezing but also you’ll look like an idiot. Spring is a risk. Realistically so is summer, but it’s a slightly more sensible risk. If you’re on holiday somewhere tropical, then you’re onto a winner.

Shoes to Wear With Shorts

What you put on your feet is actually more important than what you wear on your top half, when it comes to setting off your shorts effectively. High tops and shorts are only an acceptable combination for tall men. Flip-flops and sliders are okay in your garden and at the beach, but no self-respecting style aficionado wears them anywhere else. Depending on the occasion, canvas shoes, boat shoes and fresh white trainers are all a good bet.

Get the Fit Right

Just as you wouldn’t wear trousers that gape or squeeze at the waist, the hemline of your shorts needs to fit your leg properly. Too tight and you’ll get unsightly bulging – and this is bad news even if your legs are pure muscle. Too loose, and the fabric will flap and make your legs look skinny. Aim for slim-fitting shorts that give your legs space to move and are comfortable to sit, walk and run in.

Oliver Cheshire wearing shorts
Oliver Cheshire wearing shorts while out in Cannes


The Occasions

Now you’re thinking what to wear with shorts, and when are they acceptable right? We’re prepared to go out on a limb here and say that – event-specific dress codes aside – you can wear shorts for any occasion. Wherever you’re heading this summer, take a pair (or five) with you.


Well, this was predictable. You’re in your garden or your mate’s, the sun is shining, you’ve got a gently warming drink clutched in one sweaty fist and a questionably cooked bit of processed meat in the other. Bliss. Our barbeque outfit recommendation includes (you guessed it) a slammin’ pair of shorts.

The top three shorts styles for a barbeque:

  1. Chino shorts.

The fail-safe chino short is still around, people. Easy to wear, comfortable and on the market in almost every colour imaginable – we’re big fans. Dressed up with a crisp white shirt for the kind of classy affair that serves Pimm’s, or down with a polo shirt and flip-flops for a last-minute get-together with the pals, the appeal of chino shorts lies in their versatility.

adam gallagher wearing shortsAdam Gallagher wearing shorts and a shirt


  1. Blue denim shorts.

The girls have been bending our ears for years about how denim shorts have literally saved their lives countless times when it comes to summer dressing. Maybe it’s time we listened. By donning blue denim, you instantly look ahead of the curve in a kind of relaxed, effortless, ‘I woke up like this’ way. Pair with a loud shirt or a statement plain white t-shirt.

  1. Cargo shorts out of style? Nah.

Happily, for practical types and the devoted fans who insist they never went away, cargo shorts are back. Yes, cargo shorts are in style and they’re as epically functional as ever. The sheer number of pockets makes us SO happy and it means you will always be the legend that has a bottle opener on his person. Black, tan, navy and grey are the reassuringly sensible main colour options. Wear with a slim-fit t-shirt.

The Office

We don’t want to get you in trouble here so always think long sleeve shirts with shorts. If your job involves schmoozing heads of state or something then you probably shouldn’t rock up with your legs out. However, most offices are more relaxed than ever these days, particularly in summer, so opt for some formal shorts. If you’re apprehensive, check with the boss. If the answer’s yes, the other guys will be thanking you – and your leg liberation movement might even get you a free drink.

The Top Three SFW (Safe For Work) Shorts:

  1. Lawson Ike shorts

Chanel your inner (or outer) nerdiness with these clean-cut shorts. Wear Lawson Ike shorts to command respect from your team and stay on point in meetings. These beauts are sharpest when paired with a shirt tucked into the waistband to show them off.

nick wooster shorts and blazer
Nick Wooster wearing shorts and a blazer


  1. Twill shorts.

Twill shorts work seriously hard. The robust, high-quality fabric makes this style ideal for creative types who run around with sharpies a lot. The flattering slim fit works equally well with a relaxed polo shirt or a bold graphic t-shirt – find out what your workplace allows and push the boundaries ever so gently.

  1. Printed shorts.

Yes, really. If you’re ready to make a seriously unserious statement at work then the printed short is perfect. An all over print is smartest and most flattering. We suggest that you pair yours with a plain Oxford shirt for a preppy look – leave it untucked though.

The Races

A dress shirt and shorts are your best friend come race time. Regardless of whether it’s rowers, horses or cyclists, there always seems to be someone having a race in summer. And where there’s a race, there is a golden spectating opportunity for those of us who would rather watch someone else go through hell and back all for a shiny trophy than do it ourselves, thank you very much. Other people’s exertions can be exhausting though, so keep your cool in a pair of shorts as you make your quasi-informed commentary.

Shorts to Watch the Races in:

Chino shorts.

Think high-end barbeque wear for the races. That means that you need to go for a really well-fitting pair, preferably in a fun colour. Add a shirt and loafers and you’re ready for the Queen Anne Enclosure at Ascot. If you’re going any fancier, to abide by a dress code, then sadly you will need to put your shins away.

Smart chino shorts street style
A model and Nick Wooster show how to wear shorts


All-White Shorts

This is most relevant to chaps who are attending the Henley Royal Regatta this summer and who need some blazer inspiration. Nothing sets off the heritage feel of a striped blazer like a pair of crisp, clean white shorts in twill or cotton. A word of advice though, and we really mean this: ONLY sit on a deckchair or a picnic rug. Grass stains look terrible and they, well, stain. Don your favourite boat shoes (obviously) and you’re ready to watch some rowing.

The Wedding

Depending on how cool the people getting married are, you can have quite a lot of fun with your outfit as a wedding guest. Fancy dress themes are definitely becoming more common, and the overall vibes at most weddings are much less stuffy and formal than it used to be. That means that shorts are definitely du jour.

Paisley Print Shorts

The busy print of these shorts is wedding appropriate thanks to the cool monochrome. This means you can inject some personality into your outfit without upstaging the groom (which is terrible etiquette and should be avoided at all costs). Team with a smart black patent loafer, and a plain long-sleeved white shirt. Throw on a blazer if it gets chilly.

Pastel Colours

Summer weddings are all about the ice cream colours. The options are endless: mint green, pale pink, hell – even lemon yellow if you fancy it. For a quirky dressed-up look, team your pastel shorts with a complementary shirt buttoned all the way up with a bright bow tie to add a pop of bold colour. Go for something smart like a brogue on your feet to play up the formal side of this outfit.

model wearing pastel shorts
A model wearing pastel shorts
  1. Tailored Shorts

More traditionally formal, the tailored short is an accessible mid-point if you want to deviate from the conventional three-piece suit, but you aren’t quite ready to go all-out with colours and prints. Choose a smart black, grey or navy pair, and have fun with the finishing touches. If you keep the rest of your outfit neutral, a berry red tie and matching pocket square work a treat.

The Date

Find us a single person who loves a chilled out date – strolling, maybe getting an ice cream, happening on a vibesy bar with a sun-soaked terrace where you can get gently smashed together. Shorts were born for this kind of day, when you’re keen to impress but even keener to appear like you just threw on the first thing you found. Studied indifference is what you’re aiming for – your faithful shorts will be in their element.

The best date-day shorts:

  1. Black Denim Shorts

Now, this is genius. You know how black jeans manage to always look cool? And how they go with absolutely everything else in your wardrobe, so you don’t even have to engage your brain to get dressed? Black denim shorts do the same but for summer. You’re welcome. Grab these when you’re about to be late for your date and you need to trust your clothes to just look good without any serious input from you. Add white trainers for bonus points.

man wearing black shorts and green T-shirt
Brad Pitts loves his white shirts


  1. Polka Dot Shorts

Fun and relaxed, patterned shorts are good to go from brunch to bar. If they could speak, they’d say: “date this guy. He doesn’t take himself too seriously, has a GSOH* and looks awesome in shorts!” We can’t promise that you’ll find love with statement legwear alone, but it’s a good place as any to start.

*good sense of humour – old school dating speak from when Tinder had like a 140 character limit or something.

  1. Skinny Shorts

If you’re going all-out sexy then skinny-fit shorts are guaranteed to do the trick. This pair sits on the knee to avoid the awkward bulging scenario we mentioned earlier on, and they have a raw edge for added grunge. Pair these shorts with a loose, longline t-shirt – otherwise, you will look like you shrunk all your clothes in the wash.

The Beach

We’re going to hazard a guess that you think you already know how to dress for the beach. The trouble is – and everyone has noticed this, it’s not just us – that beach dressing has become a bit pedestrian as of late. Go back a hundred years and the very idea of a swimming costume was scandalous – but they did it anyway because they were at the seaside and they didn’t care. Where has that avant-garde, carefree attitude gone? We invite you to take your beachwear game up a notch. Leading with your shorts, naturally.

Our Favourite Shorts for the Beach:

  1. Short Shorts

The beach is one of the few places where you can truly get away with wearing daringly short shorts. Choose a pair in an unashamedly fruity print to really get the beach party started – but whatever you do, keep your top half neutral. A simple grey or white t-shirt is what’s needed to balance this look, not a Hawaiian shirt. Be warned.

  1. Swim Shorts

Yes, they count and yes you can wear them even if you’re not swimming. No longer restricted to either horrendous budgie-smugglers or overly long and baggy shorts circa ’98, we now have a choice of stylish swimwear options. Many swim shorts are inconspicuous enough for wearing around town on an average day. You know, just in case. They’re in their natural habitat on the beach though, and if you were paying attention earlier you’ll know that this is one of those rare occasions when you can freely wear flip-flops.

oliver cheshire swimming shorts
Oliver Cheshire wearing swim shorts
PHOTO CREDIT: Designs Fever


  1. Sweat Shorts

Admittedly questionably named, but brilliant in every other respect, sweat shorts are essentially shorts made from the same stuff as jogging bottoms. So you know when it’s just a bit too hot for joggers but you’re craving that level of comfort? You know what to do. These bad boys are great for the beach if you’re planning a day of sports and strolling, rather than splashing in the sea and falling asleep in the sun.

How to Wear Shorts This season

  • No matter how diverse shorts are, you need to pick the right style for your occasion.
  • Choose the colour and tone that best suits you. Taking into account your skin tone, hair colour and the colours you are wearing.
  • Don’t go tight (unless you are going for that look). You want to have full flexibility when wearing your shorts and avoid looking like you’re wearing leggings.
  • Lastly be comfortable.
Nick Wooster in blazer and shorts street style
Nick Wooster walking down the street in a blazer, shorts and smart shoes

On That Note

Hopefully, we’ve persuaded you by now that, far from being a niche choice, shorts are the staple of summer dressing. The weather in the UK is notoriously unreliable and when the sun shines, you definitely want to be able to capitalise on it immediately. Have a few pairs of shorts in your wardrobe that are good to go when the sun shows its face, and you can be the first to the bar or the beach with your legs proudly displayed.


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Here at Idle HQ, we’re on a bit of a mission. It’s a humble one but we think it’s very important. We want more...
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