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How do I know when it’s alright to leave my shirt tails out? For instance on casual Fridays, can I leave my shirt out or do I have to tuck it in? Same when meeting up with my fiancée’s parents, who are kind of casual, but also old-fashioned. On a buisness trip, can I relax and leave my shirt out after work hours when hanging with colleagues, or not? Some take their shirt out, some leave it in.

–Peter, Providence, RI

‘Manners maketh man,’ should include shirt tails etiquette. Men mistakenly think that leaving shirt tails out makes them appear more youthful. Well it isn’t true, the skinny on this myth is that loose tails make a man look fatter.  Athletes like David Beckham can get away with their shirt tails out — because who would even notice the shirt tails — nevertheless, other men in the public eye like Brad Pitt opt for keeping their shirt tails securely belted into their trousers.

With your shirt tails hanging out you would look like you were trying to still be a teenager who doesn’t know any better. Nor do you want to go for the stylishly rumpled look by wearing your tails under a jacket or with a business suit, because you’ll then look as though you pulled an all-nighter — and I don’t mean at the office.

The simple rule is this. Any shirt with tails is meant to be tucked in. Shirts with a flat bottom hem are designed to be worn untucked. However, a Hawaiian shirt or polo shirt can go either way. When in doubt, a shirt with visible tails — that is not even all the way around the bottom hem of the shirt — looks tidier tucked in.

Are you thinking about wearing a polo shirt to work on casual Friday? Tucking it in looks ever so slightly more business-like — but don’t forget to wear a belt.

The etiquette is all about getting the shirt to stay in your trousers, so make sure you buy shirts that fall at least four to five inches below the waistline of your trousers. Otherwise your shirt is likely to ride up and fold over your belt. Slim-fitting shirts are easier to keep tucked into your trousers — especially when worn with a tightly cinched belt.

Don’t get caught up in the style-trap apparent on men of a certain age, who think it’s cool to tuck in one tail and leave the other out dangling in the wind — to presumably hide their beer or wheat belly. The ‘Beckham half-tuck’ looks good only on a man in as good shape as Beckham — and especially don’t, if you’re over 25.

For detailed expert advice on the etiquette of dressing, search ‘Shirt Tails’ on The Art of Manliness at http://www.theartofmanilness.com

~Didi