But sometimes, even in the Casual Friday civilization of the 21st century, you still have to put on a nice shirt and tuck it in. For many men, the hardest part of avoiding a fashion faux pas is recognizing when they are in such a situation. Let us guide you onto the right path with this list of the top ten times that you have positively, absolutely got to tuck it in
1. Does the bottom of your shirt sink down low enough to hide your penis when you look at yourself in the mirror? Could you go out in public wearing your shirt as a man skirt? Do you look like a chick staying over at her boyfriend’s house? This is a clue. Your shirt was meant to be tucked. Either take it off, or tuck it in. Wearing a button-up with tails that hang down to your knees is not an option.
2. Funerals and weddings demand a tucked shirt. If the shirt you are wearing cannot be tucked in, you are not wearing appropriate attire. Aside from embarrassing yourself, remember that your recently-deceased Great Uncle Harold may have given you lousy Christmas presents, but he still deserves a better send-off than that baggy, crumpled-up polo from his great nephew. And no one wants to be that slovenly friend that the groom has to apologize for every time he and his wife look at their wedding photos for the next twenty years.
3. You are a film projectionist at the local movie theater. It might not look good, but you are alone in a dark room anyway, so you might as well play it safe and not risk being jeered when you ruin everyone’s movie experience by getting your shirt tail jammed in the machine.
4. Do you operate a wood chipper for a living? Tuck it in. Just do it. Trust me on this.
5. Did you find a pair of cufflinks clinking around at the end of the sleeves of the shirt you just borrowed while staying at a friend’s house? Tuck that shirt in before you humiliate yourself. And if your host picked out the shirt for you, he may be trying to give you a hint: that you normally dress like a slob.
6. If you are at an interview, your shirt should probably be tucked in. Unless of course you are at an interview for the Chippendales, in which case your shirt should probably be off. It’s the middle ground that is dangerous. No t-shirts. Figure out which scenario applies to you and then tuck in or take off.
7. Court appearance. From child custody battles to murder trials, you will cast yourself in a more favorable light if you show everyone involved in the legal process the respect of wearing a suit and tie. Nothing says “Repeat Offender” like someone who does not take their court appearance seriously enough to wear a dress shirt and tuck it in.
8. If the person you are paying to drive you around has his shirt tucked in, your shirt should probably be tucked as well. You don’t have to out-dress the chauffer, or even wear a tie, but the only people who step out of a limo in flip flops and a t-shirt are high school spring breakers with over-indulgent parents.
9. At work. If it is not Hawaiian Thursday, tuck it in. Some say dress for the position that you are trying to get, others say dress like your boss’s boss. The common denominator here is to dress for success. Not only will you project authority and look like the kind of person who should be promoted to division manager, but you will feel and act with more confidence as well. You have to get dressed and go in to work every morning anyway; you might as well play to win.
10. If you made a tragic mistake in the early-morning, pre-dawn light and stumbled out of your girlfriend’s side of the closet wearing this on your way into the office,
then you need to tuck it in; if for no other reason than to hide the fact that your shirt has crotch snaps.