Should Your Gentleman’s Wardrobe Include Shorts? (Post # 150)

Summer is on its way (at last). We plan to spend a few weeks in the tropics. So I’ve been obsessing in recent weeks about shorts. In particular I’ve been wrestling with the critical question: should a gentleman’s wardrobe include shorts? Its a great question fro the 150th post on this blog

There are a number of views on this.  On the one hand there are those who would argue that no man over 40 who is even vaguely stylish, should wear shorts unless he is poolside. Wearing shorts with a modicum of style is a devilishly tricky thing to pull off. An even if you could there is a school of thought that one ought not; it is difficult to have any gravitas when wearing shorts.  Precisely for this reason, certain gentlemen, particularly those of my father’s generation, simply would not wear shorts.  Ever.


The alternative view takes this precise argument as its starting point.  Stylish men have never taken style advice from our father’s generation and we are hardly likely to do so now. Shorts by definition would only be worn in an appropriately informal setting; the challenge is thus to wear shorts with style in those informal settings.

On the question of shorts wearing, it is a case where each of us needs to know ourselves and what we feel comfortable wearing.  However, I fall into the latter camp.  I do think that it is appropriate that a Gentleman’s wardrobe should contain shorts.

Blazer & SuitHowever, this comes with a health warning. There are some men who in my opinion should never wear shorts in public. For some it’s the expanse of pasty flesh which is your undoing, for others it is the obvious discomfort with having your lower legs exposed to the elements. For yet others it is some intangible but very obvious inability not to look like a berk in a pair of shorts.

If you fall into any of these categories, for the love of God and in the name of common decency, never mind personal dignity, please do us a favour and make a solemn oath never to go out in public with knee to ankle exposed. What you wear behind closed doors is your own business bro. However, that is my opinion.  You may beg to differ.

Shorts & Jumper

The critical question is, if a gentleman’s wardrobe were to include a collection of shorts what would be the best advice? As a fan of chinos, as you might expect, I am partial to chino shorts and have been evaluating a number in recent weeks.  Cargo shorts are also very cool.

A word to the wise: I am aware that there is a trend at the moment for rolled up chino shorts that only reach halfway down the thigh.  Quite what the attraction might be I am completely clueless. They look great on Daisy Duke, but you don’t see Bo or Luke wearing them do you?

Short shorts look fine on her….

There’s a good reason for that. If you are going to wear shorts, they should ideally end just above the knee, or just below the knee if you are aiming for a ¾ length look.

But I digress. If wearing chino or cargo shorts, how are they best worn?  If you are a bit of a dandy and it is a relatively smart informal context you could dress up your shorts with a button down shirt, loafers, and perhaps even a casual blazer or cardigan if you are so inclined.

Way too short
…but they are way too short on him

However, in most contexts, if it is sufficiently informal that the wearing of shorts is appropriate then you probably are going to want to combine them with polos and drivers. Whatever you do don’t wear them with socks.

For the ultimate relaxed look try wearing flip flops or sandals and an unbuttoned linen or cotton shirt over a tank top with your shorts. Sunglasses are optional.


If in doubt about whether wearing shorts is a good idea in your particular case try one on and then ask your better half for an opinion.  If she laughs or says, “If you wear that I am not going with you,’ you might be better opting for some comfortable linens instead of shorts in the summer months. They are nearly as comfortable and much less embarrassing.

So what do you think?  Should your Gentleman’s wardrobe include shorts?

man-pink-shorts1 For good value smart shorts try M&S, Matalan, Debenhams, Charles Tyrwhitt, or SavileRowCo.


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