Men’s fashion: how to wear shorts – and still look stylish – when you’re over 50

With legs-out weather upon us at last, summer’s sartorial dilemma arises. Grey Fox shares his tips on looking stylish in shorts, such as which colours and fabrics to choose, and where to buy

As he notices for the second week running that it’s getting warm out, a man’s thoughts turn to exposing his legs to the sun. Many, however, are reluctant, particularly as we reach our ‘maturity’. Knobblier knees, scars of previous sporting derring-do and general wear ’n’ tear, coupled with a chalky pallor, make us feel that it’s worth sweltering under trousers to keep them safely hidden.

I hope to persuade you otherwise.

One of the reasons that shorts have a such bad name in Britain is that, in general, we men are terrible at choosing suitable styles. There is a tendency to wear shorts too long, too short, too baggy, or laden with pointless pockets.

Length and cut are everything. Whatever your size and shape, I suggest that the best length for a pair of shorts is with the hem two or three inches above the top of the kneecap. Unless you are blessed with an exceptionally fine pair of legs, stick to this advice like glue.

Too short and you run the risk of looking like a groin-flashing 70s football player. Too long and you may look like something out of It Ain’t Half Hot Mum.

Baggy is neither flattering nor practical. You’ll find that the legs flap around and won’t be at all comfortable. But too skinny and they can be more revealing than you wish.

Cargo shorts are a sartorial no-no; far too lumpy and shapeless. Mountain walking or gardening are their only acceptable arenas.

Choice of colour and pattern

Instead, try patterned shorts, but ensure your upper-half attire complements them. The more complex and larger the pattern, the harder it is to do this. A vivid pair of Hawaiian print shorts will need plain colours elsewhere, or you will look like a poorly-designed patchwork quilt.

Calmer, plain colours or discrete stripes are safest, or neutrals such as khaki and navy blue. For style points, try brighter colours: cobalt blues, reds, pinks, green, soft yellow.

The best shorts are always reasonably straight-fitted, slim around the leg and waist, finish just above the knee, and are plainish in design, with no extra pockets.

Which fabric to choose

So what should your shorts be made of? To some extent, that will depend on where you will wear them. For holidays, garden and beach, (almost) anything will do: cotton twill, denim, linen (just go nowhere near those god-awful synthetic sports shorts).

Linen looks stylishly crumpled for informal wear, but not for smarter, more formal use, where crisp cotton looks best. Think Gatsby for inspiration.

To really lead the way, opt for matching shorts and jacket. Yep, a shorts suit. It can be made of wool and mohair and beautifully tailored.

Alternatively, wear shorts, of whatever colour, with a cotton blazer or summer jacket, enlivened with a jazzy pocket square.

Where to buy men’s shorts

Although autumn wear is just starting to appear in the shops, all of these currently stock shorts that fit the brief:

Oliver Spencer: contemporary yet classic pieces, with 80 per cent manufactured in Britain. Available from its stores in Bloomsbury and Soho, at Mr Porter, or see the shorts selection here.

Men’s shorts at John Lewis: the failsafe option for a good selection of mid-priced brands.

Albam, an independent with four branches including Covent Garden: simple styles, with the motto ‘Simplicity, Quality and Honesty’.

Percival Clothing in Soho: quality British-made clothing with a classic feel, many with contrasting linings, buttons and detailing.

Universal Works: another independent producing heritage-influenced pieces, set up by an ex-Paul Smith designer. Stockists around the UK and Europe. See Universal Works’ shorts range.

Which shoes to wear with shorts

Finally, there is the nation-splitting question of socks and footwear. If you wear crocs, flip flops or socks with sandals, you may well be ostracised from your community.

Deck shoes, Converse-esque canvases or espadrilles are best – and, please, no black leather footwear. If you have to wear socks, make them short, discrete, plain and pale coloured. Avoid long and white, unless you’re playing tennis.

I’m not going to rule out knee-length khaki socks, because I’ve a feeling they will burst back into fashion soon, maybe worn with light brogues to give a mid-20th-century military feel. Style is about the exploration of possibilities, after all.

So, gentleman, don’t hide those legs away. With smart shorts, sensibly chosen, you may pleasantly surprise yourself, and others. Now, pass the fake tan.