If you’ve ever bought a shirt one size too big thinking it will make you look bigger, you’re putting your look at risk. Oversized shirts make little guys appear even smaller and big guys look like they’re wearing ponchos. The surefire test for whether a shirt fits is in the shoulder: The seam should land right on top of it. Anything that sags toward your bicep was built for someone with a bigger frame. The body should skin your torso, not spill over the sides when it’s tucked in.
The ’90s were a time when low-lying bottoms were the norm. Luckily, that time has passed. So if you’re still sagging, pull your pants up to your natural waist, which is at least an inch and a half above your hip bones. If they can’t stay put, use a belt or take this opportunity to buy a smaller size. Aside from making you look more put-together, this adjustment might make your other clothes—namely your shirts—fit better. Of course, if you have especially long legs, you might opt for low-rise pants, which will lengthen your torso.
Crumpled Pant Legs
This is what happens when you wear your pants too low—or worse, don’t get them tailored. This crumpled mess can make a $1,000 suit look like a cheap sack. Cuff casual pants until they rest neatly at your ankles—any more than three folds, and you should get them hemmed. Formal pants should barely rest on your shoes (tell your tailor you want a half break). For a more modern look, cut them a bit shorter (no break) and show off some ankle, or a cool pair of patterned socks.