When did the simple act of donning a shirt become so complicated? Do you really need to be told when to wear your shirt tucked in or out? Yeah, you kinda do.
Let’s start with the obvious: It’s your shirt, your body, your call. If you want to wear all of your shirts either tucked or untucked, it is well within your constitutional rights (I checked). That said, here are a few guidelines based on the shirt, the event, the body you have, and the technique for optimal tucking.
The Shirt: Is it a dress shirt? The long-sleeved variety with “tails” that are longer in front and back that form an inverted V at each side? Most of the time, this looks best tucked in. Is it a fine cotton, silk or linen sport shirt? Buttons down the front? Could wear a tie with it if you felt like it? Same deal. Want a few tips on how to keep that dress shirt tucked in all day? Here's a great video.
Some exceptions? You have a swimmer’s build with a crazy flat stomach, or you are either 1965 Paul Newman or 2016 Ryan Gosling, in which case, have at it. If you are meeting Rihanna for pancakes at 4 in the morning, you have not only my permission to untuck, but my blessing.
Is the shirt hemmed evenly, (that is, flat across the bottom)? By all means untuck away. A little curved at the bottom, with the rounded edge of the tail cresting somewhere along your zipper line? Tuck or untuck as you see fit. What about shirts that are just meant to be more casual, like a flannel? There is probably someone in the world who could rock that tucked in, but as of yet, I have not met him. Ditto the long-sleeved rugby shirt.
There is a finer line than most of us would like to admit between being the stylish, casual guy and being a slob. If you look in the mirror and have even a fleeting question about which side of the divide you fall on, then tuck. Tucking shows a bit more effort – a little hustle, so if you’re making a first impression, it’s often the way to go.
When I was about six, I zipped up my pants then tucked my shirttails into my zipped up pants, and looked, in my father’s words, “like I was stuffed into a sausage casing.” I didn’t even know what that meant, but in the 60 seconds that followed, he taught me to put on my shirt first, pull up and zip my pants over the resting shirttails, and, importantly, put my little hands in my pants pocket after zipping, and grab the shirttails to pull down and adjust for a clean line. Don’t tuck yourself in like a six--year-old.
This final tidbit should go without saying, but I’ve seen too many violations, so here goes: If you wore a shirt tucked last week, and did not launder or dry-clean it, for the love of God, do not wear it untucked this week. You will look like you woke up in a Greyhound Station.
Here are a few of our un-tuckable favorites.