How To How To Of The Day: How To Tuck In A Shirt Properly November 29, 2015November 28, 2015 gags Enjoy! https://youtu.be/j1vaQ1B73Lg Tuck a shirt in properly and you can look as dapper as Don Draper. Do it wrong, and you’ll end up looking like Simon Cowell. Here are some handy tips of the shirt tucking variety.