Published: July 22, 2026
Read: 5 min
In: Uncategorized

Shorts

“Does my penis look small in these?”

The Anxious Shorts-Wearer’s Checklist

Style

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The sun’s out, the shorts are on, but you catch a glimpse of yourself in the mirror, and Things Look Weird. Is it your legs, or the shorts? Either way, it’s not good. Allow Fashion Director Victoria Gaiger to find the right picks for you.

The sun’s out, heat is on and now it’s time to think the unthinkable: should I wear shorts? To which, if you are going to work, there is only one answer: no (unless you happen to work as a footballer or a tennis coach). But if you are not on your way to the office, and as long as you don’t possess legs with all the spindly definition of al dente spaghetti, then the answer is, er, maybe. Just follow this handy checklist to be sure:

Do they fit? Shorts should be neither too long or too short. Aim for somewhere between halfway down the hamstrings and north of the calves.

Do they show your boxers? Underpants should not peak out of the top (or bottom!) of your shorts at any cost

Do they belong on a man of your age? Teenagers can wear them really long or at half-mast but as you add years to your birthday you need to subtract inches from your shorts. Until you reach cargo/bermuda short level, at which point stick. Once you hit 40 they are best kept just a few inches above knee.

Editor’s Picks


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albam Mountain shorts £99

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FOLK drawcord shorts £110

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FREEMANS Cotton-Twill Shorts £200

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TOPMAN SELECTED HOMME Navy Chino Shorts £35

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TOPMAN Seersucker Shorts £45

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Do you have short legs? Shorter shorts will make you look taller than you actually are. If you’re conscious of having thicker thighs, a darker colour can slim you down.

Do you have legs like Peter Crouch? As the veteran Stoke striker will no doubt know, finding a pair of shorts that suits a human bean-pole can be tricky. Your starting point is that a bold print hides skinny legs.

Surfer baggy of Bjorn-Borg-snug fit? Like the finest Savile Row suit, the cut of a man’s shorts should go hand-in-hand with his body shape and the secret is knowing basic proportion rules. Fitted/tighter shorts look good on slim men and slim shorts will make the larger man look smaller.

Are you happy with the hem? Aim for the sweet spot: the inches of space above your knee, but below your mid-thigh. Landing here will ensure your wider outfit remains in proportion. Don’t forget to add a turn up if the stitching of the hem allows.

Is that the right waist size? Don’t make the mistake of either buying the smaller size thinking it will hold it all in or a size too big to make you look less skinny. You will kid no one! Stick to your proper size.

Flip flops , low-cut Converse, Stan Smiths or sandals? All work, some better than others depending on whether you are going to get wet. But never accessorise with heavy leather shoes – you’ll just look like you forget to put on your trousers. Or boots (two words: “Village” and “People”).

Socks? Are you kidding. Do not wear visible socks with shorts unless you are off to school.

Still in doubt? Wear trousers.

 

Need something to go with those? How about a subtle Hawaiian shirt?

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