Of all the garments on a man’s sartorial shopping list, shorts are probably given the least consideration. On the whole, we tend to favour buying cold-weather clothing over summer staples. A jacket is always going to be a more pleasurable purchase than a set of flip-flops, and indulgent cashmere knitwear trumps a new T-shirt every time.

However, in the long run, this habit of treating warm-weather legwear as an afterthought can be detrimental to your style. It’s one of the key reasons why otherwise fashionable men are left scratching their heads in confusion when the sun makes an appearance and they’re faced with the prospect of having to put together a suitable outfit.

The secret: good summer dressing starts from the knees up. Which means choosing a knock-out pair of shorts is the most important style decision you’ll make between June and September. Here we break down everything you need to know – from how they should fit to the key styles to shop.

Picking The Perfect Pair

Much the same as with any other item in your wardrobe, fit is the most crucial factor when choosing a pair of shorts. Generally speaking, the hems shouldn’t sit any lower than just above the knee. Unless you’re deliberately trying to look like a member of an early 2000s pop-punk band.

Having said that, it’s fine to venture a little higher. Short shorts are having a bit of a moment right now, so feel free to go about halfway up the thigh if you haven’t been skipping your leg days. Anything more than that and you’re in dangerous territory. If you’re thicker set, stick to slightly longer styles for best results.

In terms of cut, it really depends on the style of shorts, but more on that later. As a rule of thumb, slim fit is a timeless and foolproof choice, but for swimwear a looser cut is more than acceptable.

Key Short Styles To Consider

Below you will find the three pairs of shorts any gentleman should have in their warm-weather rotation. We’ve forgone denim (not practical in the heat) and jersey (too sloppy for resortwear) to focus on those timeless essentials you will get years of wear out of and will have you oozing summer refinement.


Chino shorts are very much the bread and butter of the summer legwear world. They’re simple, eternally stylish and offer all the versatility of a Swiss Army knife. If you’re going to have just one pair of shorts, make it a pair of these in navy or beige with a slim cut. You’ll be amazed at how much use you get out of them.

When To Wear

Put simply: every day. These are your day-to-day shorts – they’ve got your back for everything from strolls across the beachfront to hitting the town for a spot of al fresco dining. The beauty of them is that they can be dressed up or down with ease. This allows you to cover the entire spectrum of social occasions with just a single pair of shorts.

How To Wear


As touched on above, chino shorts are the ultimate smart-casual style. This means the pieces you surround them with will determine how formal your look is.

To keep things smart yet summery, try teaming a navy pair with a white Oxford button-down shirt, some tortoiseshell sunglasses and a pair of boat shoes or loafers. A fail-safe look for evening meals or afternoons at the bar with friends and a bottle of wine. Roll the sleeves to instantly make things a little more laid back.

As far as casual goes, why not try a beige or dark green pair with a high-quality plain white T-shirt and some luxe, white leather sneakers?

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One of the most common misconceptions about shorts is that they’re impossible to dress smartly in. Thanks to the rise in popularity of tailored styles, this is no longer the case. So instead of sweating your way through summer in dress pants or chinos, pick up a pair of these and fill a gap in your wardrobe you didn’t know existed.

When To Wear

With their refined looks and sharp appearance, tailored shorts provide a way to dress up even when the sun is blazing. Summer dates, evening meals on holiday, garden parties – all of these scenarios call for something a little more refined than your usual warm-weather options, while still allowing your legs to breathe.

How To Wear

Brunello Cucinelli

Tailored shorts may appear to cater to a very specific niche, but they are actually surprisingly versatile. The relaxing of dress codes mean that teaming a pair with trainers and a T-shirt is perfectly acceptable

For a go-to casual approach, tuck a plain or striped tee into a pair of tailored shorts and top it off with a well-made pair of suede sneakers from the likes of Common Projects or Grenson. If the occasion requires something more formal, swap the tee out for a cotton or linen-blend shirt and the sneakers for Derby shoes. If there’s a chill in the air, don’t be afraid to throw an unstructured sports jacket on top, too.

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There once was a time when beachwear consisted of nothing more refined than a liberal coating of sunscreen and a pair of Speedos. Thankfully, those days are behind us. What we’re left with is a plentiful assortment stylish swimwear, much of which wouldn’t look out of place in city bars, let alone beach huts.

When To Wear It

The beauty of contemporary resortwear is that it’s no longer confined to just beach or pool. Brands like Orlebar Brown are making swim shorts that masterfully tread the line between beach- and bar-friendly, meaning your holiday haulage just got lighter.

How To Wear It

Frescobol Carioca

How you style your swimming shorts will depend largely on what category they fall into. There are colourful, loose-fitting options, like those offered by the likes of Onia and Frescobol Carioca. Or there are more fitted, tailored styles, as purveyed by the aforementioned Orlebar Brown.

Laid-back, patterned swim shorts are best worn with nothing but a nice, even tan. Still, they can still be teamed with other resortwear as long as it’s simple and not fighting for attention – think a breezy, white linen camp-collar shirt or polo shirt and a pair of sandals or espadrilles.

Fitted styles offer a few more options. Again, they’ll look great worn on their own around the pool. However, try dressing them up with a statement vacation shirt and some loafers or driving shoes for lunch at the marina.

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