How to Wear Shorts This Season

How to Wear Shorts This Season
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. Check out more Men’s Style Guide features and check out our store.  shopthelook 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 PHOTO CREDIT: Pinterest wearwith
  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
toppicks 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
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