If there is one style that always comes back around like a boomerang, it has to be the cuffed jean look (the young kids call it pinrolling these days).
I can't even think about when the look premiered (maybe Grease?!), but one thing is for sure is that the look is back! Now, even though a style is "back" it doesn't mean you can add it to every look or pair of jeans in your closet.
Now that I've vented a little bit, let's tackle ABC's of how to cuff your jeans.
A. Sporting baggy jeans with a cuff just doesn't give off the same clean and crisp impression (despite what your father may think). Try wearing slim or skinny fit jeans and see just how it elevates your look.
B. Keep it even. Uneven cuffs are JUST AS BAD as wearing baggy jeans with a cuff. Seriously. Take pride in your look and go the extra mile to make sure your cuffs are represented correctly.
C. Control the height. Thick cuffs give off the impression that it's your first rodeo. A cuff too big makes it seem like you are wearing a pair of jeans too big, and a cuff too small gives off the impression you aren't yet committed to the look. For the best results, leave at least 1 - 2 inches between the end of your jeans and the tops of your shoes. Trust me, you'll thank me in the end.
Take a look at these quick help videos while your dressing for visuals and assistance.
How to do it: Roll those hems up twice, but as with the "long single", be careful — this thick band can shorten your appearance from the waist down.
Denim is works with: Light to mid-weights, but something with a little more heft will look cleaner.
Shoes you should wear: Bucks, chukkas, chunky sneakers, or boat shoes... basically anything.
How to do it: Pinch a 1-2" of fabric at the side before you roll from the bottom. This tapers wider cut pants. (Check the video below for a tutorial!)
Denim it works with: Longer cuts & lighter weights.
Shoes you should wear: Sneakers and any other shoes you'd like to show off, as this will keep your jeans from obstructing the view.