MANtoMEASURE: Summer Essential - Men's Shorts

The prospect of celebrating summer might have you toying with the idea of spending many days in a pair of shorts (especially if you plan on being poolside the whole time). But going pants less is a deceptively tricky move—wrought with pitfalls and misconceptions.

Kilts, togas and tunics laid the path for the first knee breeches, which upper-crust Europeans were spotted in as far back as the late 14th century. The modern short silhouette didn’t come along until half a millennium later, when the British military was looking for a way for its soldiers to keep cool in warm places like… Bermuda. The army’s smart-looking knee-length trousers quickly caught on among civilians, spawning 100 years of sock dilemmas.

More often than not, they’re considered a necessary evil. Tom Ford famously said that a man should never wear them. That’s why shorts are probably one of the hardest items to put a decent outfit together with and this is even more obvious when you see other people “trying” to rock them. With jeans there are so many shapes, cuts and washes and you know where you stand with them. You can wear anything on the top half (formal or casual) and still easily pull it off. Shorts however are slightly different. Many men do not know how to wear shorts correctly, and do not know what items will look good with them.

First of all, as always, fit is everything. 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.

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 big camo pockets on the side and stupid pull strings that don’t do anything. Invest in a pair that looks like you’ve cut off the bottom of your chinos.

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 color. The perfect pair for any situation would be in medium grey because it compliments every other color imaginable. However, feel free to invest in a navy, camel or black pair as well.

Once you’ve got your neutrals down, start to get a bit more adventurous. Why not try some block coloring? Purchase a pair of red, yellow or green shorts and then anchor them by keeping everything else in neutral tones.

You can also 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 summer you can wear the shorts 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 pull of shorts at the office.