So this is an article I’ve been unwilling to write for the last two months. Due to the fact we appear to be experiencing one hell of an Indian summer at the moment here in England, anything sartorial with a summer tinge has been classed as a ‘holiday’ feature. However, as I sit here in a flat in London (that I am totally crashing by the way), the sun is seeping through the window and I’m starting to think I can finally cover shorts in confidence. If the weather changes, well I guess we’ll all just have to go on holiday, won’t we?

Shorts tend to be a bit of an iffy subject in the menswear world. All too often guys can stray into the ‘I’m just off to play some volleyball in my ¾ lengths, dude’ territory. Or even worse, the ‘I think my legs are amazing so I’m wearing hot pants’ look, which doesn’t help anyone. Even if you do nail the fit and style, when is appropriate to wear them? Some might say only on your days off. Others, like myself, would say wear them to the office if you want. Because, trust me, you really can and this article will show you how.

Fit Is KEY

First of all, as always, fit is everything. Similar to my article on swim shorts, you need to make sure that they end one or two inches above your knee cap. The shorts should also be of an athletic fit. By this I mean slim but not skinny; you want enough room to sit down comfortably, especially when you consider what happens to your thighs naturally when you do. Making sure that the shorts follow the shape of your quads when trying them on is a foolproof method of getting this right.

Consider Quality

Secondly, think about quality. Shorts, like any timeless item, are a piece that you are investing in because they won’t go out of fashion any time soon. All the important features that you’ll be looking for such as the waistband construction, pockets and buttons all get better the more you spend on them. When considering the waistband, make sure it is the same style your chinos or suit trousers have. The time of elasticated shorts are over I’m afraid, so buy some shorts that remind everyone that you are, in fact, a man. So I’m talking about losing the camo pockets on the side and stupid pull strings that don’t do anything. Invest in a pair that look like you’ve cut off the bottom of your chinos. More on that later.

Invest In Neutrals

If these are going to be your first pair of shorts (or you are upgrading your old collection) I would recommend buying a pair in a neutral colour. The perfect pair for any situation would be in medium grey because it compliments every other colour imaginable. However, feel free to invest in a navy, camel or black pair as well. My favourite pair at the moment is in camel because they look perfect with an untucked white shirt or with a grey polo and navy blazer.

Experiment With Colour

Once you’ve got your neutrals down, start to get a bit more adventurous. Why not try some block colouring? Purchase a pair of pink, yellow or green shorts and then anchor them by keeping everything else in neutral tones. I often wear my pink pair with a nautical-inspired striped navy Henley and some black penny loafers or blue boat shoes and get complimented every time.

Or perhaps you’re more of a pattern kind of guy? That’s fine too because the same principal applies. Why not try some blue vertical stripes, a red gingham check or maybe even some madras shorts? Just remember to keep your top half solid and you can’t go wrong. Or if you do want to pattern mix then make sure that the width/size of the patterns – say stripes and checks – aren’t too similar to one another and you’ll be fine.

In The Office

But when should you wear these newly purchased shorts? Well, the answer is everywhere! Your shorts will look great with a simple tee or polo and equally as good with a shirt, tie and jacket because you’ve nailed the fit already.

If you want to wear shorts to the office, make sure that you keep everything formal to compensate. Like I said, good quality and tailored shirts and suit jackets will go a long way but don’t forget your footwear either. I would recommend a proper shoe – wingtip, cap toe or double monk strap and never brand new. Go with brown rather than black and skip the socks (at least those that show). Belts are fine but not essential in my opinion. This, combined with a confidence on wearing the shorts, is all you need to pulling of shorts at the office.

Note: This look can translate well to a night-out, just lose the tie or swap the shirt for a polo.


Finally, a point on cutting your losses. All those old ill-fitting chinos you have collecting dust, why not turn them into shorts? You could do this with a pair of scissors and a ballpoint pen or take them to your local tailor. It’s a simple procedure that shouldn’t cost more than £30. Just make sure you get the length right beforehand. You can do this by drawing a line around the trousers with some chalk because, hey, it’s what the professionals use, right?

So there you have it guys – a beginners guide to real men’s shorts. Once you feel you’ve got these down you could start moving into bolder prints like floral or even two tone colours. But that’s any other article for another day.