Whether you’re heading out to climb a mountain or the corporate ladder, it’s nice to know you’ve got some basic details confidently covered. One incredibly basic detail we all face: knowing when or how to tuck in shirts. Thankfully, there are a few rules you can follow (or break) with confidence.
If the hem (bottom edge) of the shirt includes tails (longer in the front and back, shorter at the sides), it is designed to be tucked in. (Like most men’s dress shirts.)
If the hem of the shirt is even or straight across, it is usually meant to be left untucked. (Like graphic t-shirts.)
Here’s where the hem rule may be overruled. Consider the nature of the fabric. A soft flannel shirt lends itself to being left untucked; properly fitting chambray shirts or polo shirts can work well either way, and a crisp Oxford dress shirt just begs to be tucked in.
Where are you headed? If you’re going to a business lunch, a job interview, or to meet your grandmother for brunch: tuck in your damn shirt. Heading to a tailgate, the game, or a pub crawl? Enjoy some laid back fun, and don’t worry about the shirt tucking.
First Things First
Before we address how to tuck in your outer shirt, let’s point out one foundational step: if you are wearing an undershirt, tuck it into your underwear. This ensures that only your outer shirt will be tucked between your underwear and your pants, and this will go a long way in helping that shirt stay tucked in. (For the record, no, you should not tuck your outer shirt into your underwear. You don’t want your “Kiss Me, I’m Irish” boxers creeping up and peeking out the back of your waistline, do you?)
The basic tuck lives up to its name. Simply get dressed in the right order, and you’re pretty much done. Put on and button up your shirt, then pull your pants or trousers up, buttoning them over the shirttails. Be warned, though: this really only works well with a very fitted shirt. Anything else is going to require a bit more attention to avoid looking sloppy. (If your shirt looks “blouse-y” or loose after you’ve tucked it in, you’re not finished. See below.)
The military tuck may require some practice, but the result will be a sharp looking shirt. Start with a basic tuck, but keep your pants unbuttoned at this point. Grab hold of any excess fabric at both sides of the shirt (pinch along the side seams), and pull down to make the fabric taut. It ought to be tight enough that it’s smooth across your chest. Then, fold the side seams toward your back, pinching them to make a sort of side pleat. Finally, button your pants and belt them to hold the pleats secure, just behind your hips.
A final note: whether you tuck or don’t tuck, be sure to start with a shirt that fits you well, and you’ll already be ahead of the game.