A reader asks - Should I tuck in my shirt or not?

Let's have a brief respite from the Grey Fox Made and Designed in Britain Month.

From time to time I am contacted with sartorial questions by visitors to the blog. Usually I can give my view without too much problem. Then, recently, the question arrived (from a Spanish visitor) that I had been dreading – should the shirt be tucked into the trousers or allowed to hang outside?

I’d been dreading this question because it exemplifies the confusion about his dress sense that a man feels when he reaches middle age - am I trying too hard, is this too young a style? A young man would not be concerned. Once middle age approaches, however, that confidence is undermined. Some months ago, in a crisis of confidence, I made the mistake of asking my children for advice on this knotty point. My daughter said the shirt should be tucked in, my son disagreed.

At that point I recalled why I had started Grey Fox; to find my own way on matters of style through trial and error. I had to answer this for myself. So, here is my carefully-considered view. As ever, I emphasise that it is my view. You should decide for yourselves (all images from Mr Porter):

Formal shirt, Brioni Bengal stripe - Mr Porter

Formal shirt –

1. Always tuck in your shirt when worn in a formal situation, with a suit, jacket or tie.

2. By all means, wear it outside your trousers if worn informally (for example with jeans), but only if,

• The shirt is cut suitably, i.e. it is not too long or so baggy that it whips around your hips like a country smock. Best is a slim-fitting shirt that is not too long or over-generously cut at the bottom.
• You are not wearing a tie.
• You feel it looks right. I know that this sounds unhelpful, but you need to stand in front of a mirror and ask yourself, ‘Do I feel uncomfortable like this? Will I feel self-conscious all day?’ If so, tuck the shirt in.
• You have taken advice which is unanimously in favour of the shirt being untucked. However, be warned, if you ask for advice you run the risk of receiving half a dozen conflicting opinions which will only leave you confused and even hurt (avoid asking teenage daughters for advice if possible).
• The shirt is not rumpled at the bottom because you have tucked it in and then changed your mind. It should be neatly pressed from top to bottom.

Casual shirt untucked. Dunhill denim - Mr Porter

Casual shirt tucked in. Rag and Bone - Mr Porter

Polo shirts –

Can be tucked in or not. I generally wear them untucked, but I like wearing them with a summer blazer, in which case they are tucked in (I'm not a fan of untucked shirts with jackets). As with formal shirts, make sure the cut is not too long or baggy if it is to be worn outside the trousers.

T-shirts –

Generally will not be worn tucked in, unless they are worn as undershirts. If you have massive upper body musculature and like to show off, tuck the T-shirt in, I'm not going to try to dissuade you.

A cunning tip

If you're still unsure, try having your shirt half tucked in. This requires great subtlety (and sprezzatura) if it is not to appear too contrived and if you are to avoid looking like an overgrown schoolboy who's just climbed a wall to steal some apples. Practice makes perfect with this one.

(Glossary - For some readers trousers are pants; for UK readers, if you feel you need to tuck your shirts into your pants (underwear) you are visiting the wrong blog).