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.

Buying Considerations

It’s always a good idea to put some careful thought and consideration into any new clothing purchase. Shorts are no different.

In order to ensure you end up with a pair of shorts that look good, feel good and last well, there are a few key areas to consider. Use the following points as a checklist before parting with your hard-earned cash.

Fit

As is the case with any item in your wardrobe, fit is the most important factor. A lot of this will depend on what type of shorts you’re buying (more on that later) but for a rough frame of reference, opt for a loose cut for active pursuits and slim or regular cut for general wear. Avoiding anything marked ‘skinny fit’ is always good practise. You’re a grown man, not a teenager from 2005.

Length

Short length has long been a hotly debated topic in menswear for as long as there have been shorts. Trends over the years have seen the preferred length veer between extremes, but to make sure your shorts are on the right side of history it’s best to aim somewhere in the middle. Anything from just above the knee to about a third of the way up the thigh is generally safe territory.

Material

Choice of material will be based largely on the intended use of a pair of shorts. Lightweight, stretchy fabrics are better for active use, while cotton- and wool-based fabrics tend to be better suited to general day-to-day dealings. Consider temperature too. You might like the look of those denim shorts but are they really going to be practical during the height of summer? Probably not.

Quality

Last but by no means least, opting for a a high-quality garment is the best way to ensure comfort and longevity. This may mean paying a premium but if you buy cheap, you’ll often end up buying multiple times, making it more expensive in the long run. The best way to ensure quality is to research brands. Check out where their shorts are made, what they’re made from and if they offer a warranty on their products.

Key Short Styles To Consider

Below you will find the key short styles any gentleman should have in their warm-weather rotation. From activewear to smarter options, these are the types to consider.

Chino

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

Reiss

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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Tailored

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 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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Athletic

Nobody at the gym wants to see you using a Thighmaster in your boxer shorts, no matter how well toned your quads are. That’s why it’s a good idea to invest in some above-the-knee legwear for your workouts too. These sorts of shorts will usually be stretchy, comfortable and designed to offer maximum freedom of movement. This makes them perfect for exercise, but also for general weekend duties if you pick a stylish pair.

When To Wear

Athletic shorts are informal by nature. If the setting is anything but completely relaxed, you should probably opt for something else. Obviously, the gym or sports field is athletic shorts’ natural habitat, but they can also work well casually as part of an athleisure-inspired outfit. Ironically, they’re also great for lounging around in on lazy days at home.

How To Wear

Castore

The obvious answer is with your workout gear. Stick a pair on with a technical T-shirt or hoodie and top it off with sneakers or running shoes. Simple enough, but where things get slightly more complex is when you begin to venture out of the gym.

Athletic shorts can be great for laid-back weekend duties, but you should always avoid pairing them with anything too smart. A polo shirt and canvas sneakers is fine; an Oxford shirt and Derby shoes, on the other hand, is not. Stick to teaming them with pieces that are in some way sportswear related and you should be fine.

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Swimming

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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General Styling Tips

Don’t Go Top Heavy

Mango Man

Styling a cohesive outfit is largely a balancing act. Every element needs to work in synchronicity and there should be a general sense of unity from head to toe. This is why wearing bulky items on your top half is never a good look with shorts. Doing so throws things off balance, creating a top-heavy look that won’t do your legs any favours. Instead, stick to light fabrics and form-flattering cuts.

Choose Socks Carefully

Sock length is a tricky thing to get to grips and a lot is down to personal preference and the type of footwear being worn. While there are no hard and fast rules, we find no-show socks to be a good option across the board from a style standpoint. Trainer socks are best left alone for anything but the gym and anything above the ankle should be tasteful and venture no higher than just below the calf muscles.These taller socks are best reserved exclusively for sneakers and never for smart shoes.

Get The Shoes Right

Luca Faloni

To get an idea of the importance of footwear, just imagine wearing a pair of shorts with Chelsea boots. Suffice to say it wouldn’t be a good look. Generally speaking, low-cut shoes tend to look better, with the exception of some high-top sneakers. If it has the word “boot” in its name, give it a wide berth.

Consider Your Build

We’re all different. What looks good on one person might look terrible on another. General styling advice is useful up to a point but it’s also important to consider your own unique body shape when taking it on board. Short men should avoid excessively lengthy shorts in favour of slightly shorter styles which make the legs look longer. Vice versa for tall guys. If you have very muscular legs, opt for loose fitting styles over anything too fitted, or if your legs are on the skinny side, do the opposite.

Less Is More

Reiss

We’re firm believers in a less-is-more approach in all areas of menswear and it holds true for shorts too. Simple, understated styles age better, offer a greater degree of versatility and encourage good dressing without having to rely on zany prints or excessive detailing. And if it has anything more than four pockets, steer clear.