The mature man’s guide to wearing shorts

Chino shorts from Samuel Windsor

Get the fabric, fit and style right and you can wear shorts at any age
Image source: Samuel Windsor

Who says men over 40 shouldn’t wear shorts? Your age is irrelevant; it’s hot and you don’t want to wear trousers – what else would you choose? But if you are on the far side of forty, it’s particularly important to get the fabric, the fit and the styling right.

Here’s your guide to men’s shorts – everything you need to know to wear yours with confidence.

Best length for men’s shorts


Ideally, shorts should finish an inch or two above the knee.
Image source: Samuel Windsor’s summer chino shorts 

Plenty of fashion pundits say middle-aged men should avoid shorts. While that’s nonsense, with maturity comes a sense of refinement. You wouldn’t want to make the same fashion mistakes you made when you were a callow youth.

It’s important to get the length right. As Dennis Green writing for Business Insider UK says:

Since there’s so little fabric to shorts to begin with, the details have to be exactly right. That includes length and width.

Matt Allinson writing for Fashion Beans says: “Ideally, they should finish an inch or two above the knee.”

That said, if you’re tall and slim, you can afford to allow the hem to come within a couple of inches of your kneecaps; if you’re short, give yourself a longer silhouette by opting for an inseam that’s an inch or so shorter.

Best fit for men’s shorts

Samuel Windsor's pleated chino shorts in mushroom

Chino shorts can be flat-fronted or pleated.
Image source: Samuel Windsor’s pleated chino shorts in mushroom

David Evans, aka Grey Fox, writing for The Guardian says: “Older men and shorts can mix well if suitable styles are chosen. There is a tendency to wear shorts too long or too short, too baggy or laden with pockets.”

Avoid voluminous shorts that viewed from the side make you look like a hovercraft. Equally, slim-fit variants can give you the appearance of being trapped inside a sausage casing. The watchword here is “tailoring”.

Finlay Renwick writing for Esquire says: “For style, a simple chino with two pockets is a steady favourite.” You want your shorts to follow the line of your legs while allowing you room to move.

If you’re lucky enough to have muscular legs, you can afford to wear shorts of more generous dimensions – the last thing you want is the fabric “grabbing” at your thighs each time you stand. That’s not a good look.

Flat fronts create a simple, streamlined outline which is great provided you’re in good trim. If you’re a more amply proportioned gent, we suggest a single or double-pleated short will be more comfortable and flattering to your physique.

Shorts with turn-ups

If you’re like many men, and your legs are on the skinny side of slim, opt for shorts with a folded hem that adds bulk to your thighs.

Those with big legs will look better in shorts with a clean, unadorned hem, the same applies to anyone who’s below average height – a leaner outline accentuates length rather than breadth.

Best colour for men’s shorts

Samuel Windsor's chino shorts in plum-model2

Blue is a versatile option but pastels make a sophisticated alternative
Image source: Samuel Windsor’s chino shorts in plum

Get your legs out as early in the season as you can – preferably in the back garden at home. You’re not after a deep tan, but prison pallor and shorts are not a good mix. Beware burning, but if you can achieve at least a pale magnolia finish before wearing your shorts in public, so much the better.

As for the shorts, leave patterns to younger men, and stick to classic tailored versions in muted colours. Tan and oatmeal, or navy are a good place to start, but if you’re feeling more adventurous, pastels look good, as do darker browns and crimsons.

Stick to natural fabrics like cotton and linens which will keep you cool and fresh in warm weather which, after all, is the whole point of wearing shorts in the first place. Looking for something even lighter? Try seersucker shorts in the next heatwave – smart, cool, lightweight and crease-free.

What shirt should you wear with shorts?

Short sleeved linen mix shirt from Samuel Windsor-model4

A short sleeved shirt looks smart with navy shorts
Image source: Short sleeved linen mix shirt from Samuel Windsor

For most, shorts are purely casual attire, in which case wearing a t-shirt or polo shirt is perfectly acceptable. For smart casual use, forget office shirts – instead look for cottons or linens with a slightly more informal cut.

When considering whether to wear your shirt untucked, do factor in your height and body shape. Tall people should untuck to balance their top and bottom halves; shorter men look better with their shirts tucked in. If you’re smallish but prefer the look of an untucked shirt, go for one that’s fairly short in the body.

Larger men generally look best, and are more comfortable in looser fitting shirts worn outside the waistband.

What shoes look best with men’s shorts?


Classic deck shoes work perfectly with shorts.
Image source: Samuel Windsor’s classic deck shoes

Wear your shorts with deck shoes or loafers – both have a low top line which accentuates your ankles. Go for ankle socks or invisible socks – the sans-socks look is stylish, but it’s also uncomfortable and makes your feet stink.

Alternatively, why not take your footwear cues from the British Army? World War II saw British officers combing the bazaars of Cairo in pursuit of something comfortable to wear on their feet. The result was a lightweight suede boot with a crepe sole. A legend was born – wear your desert boots with ankle socks and a pair of khaki chino shorts.

Posted in Men's style guides.