Introduction

With the official beginning of British Summertime (and the inevitable going forward of the clocks) looming ever closer, I’ve begun putting some serious thought into making the transition from my autumn/winter wardrobe to a brand new spring/summer version. It often starts slyly; a subtle introduction of linen or madras here, a touch of socklessness there. But sooner or later, we all have to start bringing out the big guns. And there is no gun bigger than shorts to sound the charge on long evenings, beer gardens and never ending hose pipe ban rumours.

But first – before we discuss why it’s perfectly acceptable to start wearing shorts as early as April – we should cover some ground rules. Whether you’re a seasoned pro or a style beginner, it’s always nice to have a few guidelines to go by. Especially with an item that can make or break your look.

Men’s Shorts Guidelines
  1. Nail the fit – this is the biggest problem with guys and shorts. Most men seem to pick the baggiest, roomiest pair they can find, which is rather unflattering. Instead, you should be looking for a pair that fits you well in the rear/thighs and that ends around an inch above the knee.
  2. Keep it simple – both in regards to accessories and colour. If it’s your first venture into proper shorts, then stick to neutrals such as white, navy, grey and beige. Reds, greens and yellows are still fair game but will be easier to work into a look if kept in a pastel tone and a solid block colour. As for stupid toggles, zips and pull-cords… just don’t. Nothing will make you look more lacking in style than some shorts that look like you were confused about how to put your own parachute on.
  3. Bigger picture – always bear in mind what you’re going to be wearing with your shorts. Often it’s all too easy to get caught up in the awe of your new pink ones (or an old pair you forgot about) and then throw on whatever’s close to hand on your way out. Try to pay attention to the colours and the cut of the other pieces you pair them with, and make sure they both compliment your shorts.
  4. Confidence – some guys shy away from shorts for the fear of showing too much leg. As long as you stick to the standard length and fit mentioned above, it’ll be fine. Show some courage and go for it.
When To Wear Shorts

So why shorts so early? Well, honestly, why not? As soon as the weather warms up, everyone ditches their layers and feels fine in just a t-shirt and jacket (or some variation on it). Why not just invert the look? In my eyes there’s nothing wrong with an outfit that consists of a cotton shirt, merino wool jumper/cardigan and a pair of tailored shorts – it can often be seen in the spring/summer lookbooks for brands such as J Crew and GANT.

The key is, as with anything in a seasonal wardrobe, to pick the right kind of materials. Seeing as it’s only the beginning of British Summertime, why not start with some slightly beefier cottons or herringbone wools? Pair materials of similar texture with them such as Oxford cloth/flannel shirts and lightweight wools for the best effect.

Save those linen, seersucker and thin cottons for a few months down the line – and when you do break them out, pair them with chambray or madras shirts, linen ties or cotton-blend jackets.

  • Topman Dark Blue Oxford Tailored ShortsTopman Dark Blue Oxford Tailored Shorts
  • Topman Tmd Navy Herringbone Tailored ShortsTopman Tmd Navy Herringbone Tailored Shorts
  • Asos Cord ShortAsos Cord Short
  • American Apparel Dovs Corduroy ShortAmerican Apparel Dovs Corduroy Short
  • Topman Grey Herringbone Tailored ShortsTopman Grey Herringbone Tailored Shorts
  • Topman Navy Cord Tailored ShortsTopman Navy Cord Tailored Shorts
Individualise Your Shorts

If you fancy being really adventurous, why not make your own? Or, you know, get your tailor to make you some. You know those tweed trousers you wore the hell out of the last two years with the fraying hems? Any decent tailor can transform them into a pair of shorts ready for your transition into spring.

This is a great option for you thrifters out there, as you could easily pick up a pair of unwanted chinos or trousers for a couple of quid and get them altered to look like you paid 10 times the price for them.

How To Wear Shorts

Essentially guys, so long as you nail the fit of your shorts, stick to logical colour combinations and keep things season-conscious through the materials you pick, there is no reason you can’t start wearing shorts the moment you begrudgingly wind that hour hand forward.

Remember to keep an eye on the rest of your outfit and choose your footwear carefully. I find it best to stick with a more casual type of shoe – whether it be suede brogues, leather penny loafers or a bog standard boat shoe – but experiment to find out what suits your personal style the best.

If you just can’t bring yourself to go sockless, at least invest in some ankle/loafer socks to avoid any ghastly sock to skin contrast. Like my tailor always says – ‘when there are leaves in the trees, my ankles will feel the breeze’.

Neutral Shorts Lookbook

Let’s finish with some lookbook inspiration, to show you just how versatile shorts really are:

Men's Neutral Shorts Lookbook

  • Uniqlo Men Chino ShortsUniqlo Men Chino Shorts
  • Cotton Shorts Spot-w By Boss BlackCotton Shorts Spot-w By Boss Black
  • Allsaints Mitre ShortsAllsaints Mitre Shorts
  • Reiss Prom Tailored Shorts RhinoReiss Prom Tailored Shorts Rhino
  • Reiss Keel Denim Shorts WhiteReiss Keel Denim Shorts White
  • Woolrich Khaki ShortsWoolrich Khaki Shorts
  • Richard James Tailored Slim-fit Linen-blend ShortsRichard James Tailored Slim-fit Linen-blend Shorts
  • Austin Reed Khaki Wrinkle-free ShortAustin Reed Khaki Wrinkle-free Short
  • Asos Denim Short In BlackAsos Denim Short In Black
Coloured Shorts Lookbook

Men's Coloured Shorts Lookbook

  • Ymc Cinch-back Linen-blend ShortsYmc Cinch-back Linen-blend Shorts
  • Allsaints Corduane Damascus ShortsAllsaints Corduane Damascus Shorts
  • Topman Red Chambray Tailored ShortTopman Red Chambray Tailored Short
  • Villain Chino ShortsVillain Chino Shorts
  • Allsaints Mitre Deck ShortsAllsaints Mitre Deck Shorts
  • J.crew Stanton Slim-fit Cotton-twill ShortsJ.crew Stanton Slim-fit Cotton-twill Shorts
  • Asos Denim Short In YellowAsos Denim Short In Yellow
  • Levis Country Green Waterless ShortsLevis Country Green Waterless Shorts
  • Polo Ralph Lauren Green Cotton Chino Preston ShortsPolo Ralph Lauren Green Cotton Chino Preston Shorts