Women have been rolling their pants for years, but these days, it’s a popular look among guys too. But pulling off this style maneuver takes a little know-how. Do it wrong, and you’ll look like you’re about to wade through flood waters. First off, roll jeans, chinos or canvas pants, but not trousers, please. And make sure your pants are long enough to begin with so that the cuff ends up just above the ankle, not higher. Also, the look works well with low sneakers, loafers or dress shoes, but not socks (invest in some no-show socks to keep shoes fresh). A few cuffs to try:
The Double Cuff
Do a small cuff, then roll it up again, aiming for about a 1.5-inch cuff, no more. It should look a bit imperfect, so loosen and adjust as necessary.
The Simple Cuff
Make one cuff of about two inches, then fold the hem in toward the pant leg. Smooth out the cuff to create a uniform look.
The Pinroll Cuff
Wider pants can be pegged by doing a pinroll: Take the inner inseam of your pants and pinch it, pulling it out. Next, fold it over, so it overlaps the fabric of your pants. Grab the bottom of the pants where it overlaps and cuff it up once. Next, cuff it again, making sure to tuck in that overlap. If your pants are quite narrow to begin with, avoid this look. It will look too tight overall—and you’ll be in danger of cutting off circulation to your feet. Alternatively, if your pants are really wide, avoid this as well. You don’t want to look like you’re wearing Hammer pants. A moderately tapered style works best.
The Deep Cuff
Take the hem of your pants and make a large cuff of about four to five inches. This look evokes construction workers of yesteryear and works best with boots or high-tops.