Your shirt: should it be inside or outside of your pants? A vexing question indeed. The choice itself often has to do with the image you want to project. It should be self-evident that tucking your shirt in often gives off a cleaner, more professional look, while leaving it untucked projects a more carefree, laissez-faire attitude. There are however a few guidelines that, in most circumstances, should be followed.
If you’re wearing a tie, tuck your shirt in.
This is fairly obvious, yet some people feel that the “business in front, party below the waist” look can work. These people are wrong. Wearing a tie with an untucked shirt looks unusual at best, as the tie is supposed to drop right to your waistline. An untucked shirt obscures your waistline and inevitably makes your tie look too short. If you must untuck your shirt in a tie-wearing situation, say at a wedding where you are dancing up a sweat, then take off the tie. There is no reason to leave it on at this point.
If you’re wearing dress slacks, tuck in your shirt.
Similar to the tie, dress pants kind of necessitate that you tuck in your shirt. Dress pants look unusual with an untucked, button-down shirt. Those viewing your sartorial choice might ask, “why did he even bother wearing those nice pants if he won’t bother to tuck in his shirt?” An exception in this case can be made for a polo shirt, though it needs to be the perfect size to keep it from looking off while untucked.
If you’re wearing jeans, use sound judgment.
Jeans imply a casual nature, even designer jeans to a degree. Thus, you ought to do what looks best. This requires a mirror and a sound opinion (yours or otherwise). Tucking your shirt in with jeans can make you look sleek or make you look like you’re headed to a rodeo, so choose wisely.
If you’ve forgotten your belt, don’t tuck in your shirt.
This seems silly, but putting your beltless midsection on display will not go unnoticed. Open, naked belt loops just draw the eye. Older men in particular, for reasons unknown, will not hesitate to walk up to a complete stranger and ask them where their belt is. If you’re wearing a tie and have forgotten your belt, you’re in quite the pickle. We recommend losing the tie, and untucking your shirt, or keeping your jacket buttoned at all times to obscure the shameful fact that you forgot your belt.
If you’re wearing a sports jersey, don’t tuck it in.
Just don’t do it. It looks ridiculous. (Unless you’re actually playing an organized sport that requires it and the jersey is yours, not Bo Jackson’s.)
There you go. The glaringly obvious have been left off this brief guide as to avoid insulting your intelligence – things like don’t tuck in your sweater, don’t tuck things into your elastic waistband, etc. Of course, any rule can be broken. If they couldn’t, we’d likely be walking around with muttonchops, puffy blouses, and large buckles on our shoes to this day. Just be sure to look at yourself and ask, “am I really pulling this off? Really?” Never lie to yourself.