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A Gentleman’s Guide to Wearing Shorts

Growing out of shorts, once upon a time, was one of the many things that separate boys from men. Gentlemen, of course, would never wear shorts - except when they were in the tropics, or when they were out for a game of tennis.

But that was then.

Now, shorts are a more acceptable part of a man’s wardrobe. But the old problem still persists - how to wear a short and not seem like a preteen.

In short, how to wear a short like a gentleman?

soldiers wearing shorts WW 2

You can take the right pair of shorts to a war

Even today, there are influential voices that express severe disapproval at gentlemen wearing shorts. Tom Ford famously said that shorts are ‘never appropriate’ - not even on the hottest day of a warm summer. However, he made an allowance for the beach and the tennis court.

We will reject this as an extreme position, and explore some ways in which a modern gentleman can look perfect in a short.

1) Mind the Context

The first thing to consider would be WHY and WHEN of wearing a short - the reason and occasion.

Cool Shorts for Men

Cool Shorts for Men

Are you going outdoors on a warm day?

Are you relaxing on a weekend and feel laid-back?

Wearing shorts outdoors when the temperature is 70 degrees is perfectly acceptable, or when out barbecuing on a weekend afternoon.

DON’T wear them to a business meeting or to your office. (I worked briefly in a place where we were allowed to wear shorts on Fridays).

2) There is a Right Fit..

... And there is a wrong fit. Too relaxed or baggy, and you will look like a chicken. Too slim and skin-tight will not look good either.

A close fit and a straight fall are de rigueur for gentlemen - preferably in a variety of shorts that can be worn with a leather or canvas belt. However, similarly fitting Bermuda shorts with drawstrings are acceptable too.

3) How Long Does it Go?

When it comes to the length of shorts, gentlemen will draw the line just right. The knees should be just visible - this is the thumb rule to follow. Anything below knees would move into the “capris” territory - and should be actively avoided by a self-respecting gent.

shorts too short

Please Don't Look Like This!

Shorter versions - that show off the (hopefully) well-toned thighs should be reserved for the jogging trail or the gym.

4) Material Difference

Having established that shorts are to be worn in a certain environment and at certain occasions, it is easy to see what kind of fabrics will suit a short.

well matched shorts

Shorts, Well Matched!

Lightweight and breathable fabrics - is the mantra when selecting a short.

Linen, cotton (seersucker and Madras are the best), and chinos will get an aye vote.

Denim, nylon and wool are best avoided.

5) Colors, Patterns and Style Matter Too

Solid colored shorts in khaki, tan, olive and navy can never go wrong.

relaxed shorts

Relaxed Shorts

Patterns need to be handled with care - especially plaid and Madras checks. Thin stripes are safe, so is a herringbone pattern.

Polka dots, cartoon motifs, and floral patterns should be left strictly for the beach.

In terms of styles, cargo shorts should be better left alone - or reserved for trekking. Pleats look good only on tailored shorts that are worn with leather belts and dress shirts.

6) Finishing the Look

To complete a dashing look in shorts, a gentleman will also need -

shorts plus accessories

Shorts Plus Accessories

- shirts (half sleeved shirts - if you insist on button front, and solid-colored polo shirts)
- shoes (boat shoes, casual penny loafers, canvas plimsolls or sneakers, moccasins) - without socks
- belts (leather, webbed, canvas)
- other accessories (leather or cord bracelets, stylish sports watches, shades)
- some attitude.

That’s all, folks!


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