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Like choosing black shoes over brown, knowing whether to tuck in your shirt seems like a simple proposition, when in fact it’s not. On the one hand you don’t want to look like an uptight nerd, and on the other, you don’t want to look like a slob. You also want to be comfortable, and an arctic breeze up the back of your shirt or a whole bunch of fabric bunched up under your jeans can really get in the way of that. Here’s how to navigate this tricky circumstance for optimal style and comfort, in any situation.
Look at the shirt itself, particularly the hem.
If the shirt hem is even, it lends itself to being untucked. Be careful when leaving a shirt with an uneven hem untucked. If the shirt fits you really well, it can work, but it’s a risky move, particularly if the shirt is not the right length. The ideal length for an untucked shirt is something that hits the middle of your back pocket or the zipper of your pants. Kanye West ignores this rule, but you should not. Also look at the fabric of the shirt. Shirts in casual fabrics like denim and flannel feel right when worn untucked, while broadcloth or poplin shirts might feel more appropriate tucked in.
Consider where you’re headed.
Have you been invited to the White House? Meeting your girlfriend’s parents for the first time? Going on a job interview? Tuck in your damn shirt. If you’re not wearing a shirt that looks good when it’s tucked in, you’re probably underdressed. The same is true on the opposite end of the spectrum. Baseball games, bachelor parties and bar crawls are times in your life when you’ve earned the right to wear an untucked shirt. Do it up right.
Figure out what layers you’re working with.
If you’re planning to wear a blazer or a sweater over your shirt and that shirt has a collar, tuck it in. If you’re working with a T-shirt or a Henley, you can go both ways depending on the fit of the shirt. More than anything you want your layers to look strategic—not like you’re wearing everything you own in order to stay warm. Don’t tuck your sweater into your pants unless that sweater is made of a beautiful and lightweight material that makes it feel more like the world’s softest T-shirt.
Observe general rules of formality.
We’re pretty sure we don’t have to tell you this but let’s just play it safe. If you’re wearing a tie, you need to tuck in your shirt. If you’re wearing some type of vacation shirt or sports jersey (no judgment, but kinda judgment), do not tuck in your shirt. In both cases you’ve already committed yourself to certain level of formality and you should just let your outfit exist in that space.
And one last thing: Never untuck a shirt you’ve been wearing tucked in all day long. You will look like a guy who hates his job, which is not the message we know you’re trying to send with your outfit.
By Megan Gustashaw