It might seem like a question that a thirteen-year-old boy would ask before going to his first formal dance, but there really is a proper method to tuck in a dress shirt that will result in the cleanest finish.  The trick is in the pleat.

Why Pleat Your Fabric?

Haphazardly tucking in all the excess material of your shirt into your pants results in awkward lumps of fabric protruding within the pants and an unkempt mess of billows overflowing the waistband.  Instead, make a clean pleat in the back to deal with the excess material. The pleat will not only leave a flat, clean outward appearance, but will allow the shirt to lie flat inside the pants.

How to Make a Pleat

Once the shirt is on and buttoned, pull it firmly at the bottom in the front to straighten the shoulder seams.  The pants should remain unfastened to allow more room to tuck in the pleat.

To make the pleat, visually note where the center of the tail of the shirt is in the back of the shirt.  Pinch a handful of fabric to the left of this centerline, fold toward the center, and smooth to flatten.  Next, pinch a handful of fabric to the right of this centerline, fold toward the center, and smooth to flatten.   The size of the pleat will depend on how much excess material the shirt has.  The object is to create a flat box pleat with the excess material. The shirt should fit snugly against the body when the pleat has been created.

This tidy pleat should be carefully tucked into the unfastened pants and smoothed until it is lying flat against your body.  Fasten the pants aligning the buttons with the center front of the pants.