There seems to be as many ways to cuff and roll your jeans as there are washes, fits, and styles. With so many options, which one is right?
A better question would be, "Which one is right for you?" The worst thing a cuff can do is appear entirely too forced. You shouldn't buy into a cuff just because it's the trend, and just because a certain cuff is a trend doesn't mean you shouldn't have some fun with it. If you're not sure, grab a full-length mirror and a trusted friend, and indulge in a little dress-up.
While you're playing around, do keep some things in mind. Any style cuff should lift the bottom of your jeans up off the floor. A simple upturn of the hem is an easy and demure looking way of making this happen. Make sure cuffs fall at the same point on both legs and try not to roll up super skinny jeans -- nothing will cut off the circulation of blood to your feet faster and make you look more silly doing it. Lastly, be careful with cuffing boot cut jeans -- geometry most likely won't be on your side.
The easiest cuffs to pull off are the upturn mentioned earlier, the wide cuff and the trim cuff. Make the wide cuff by folding your hem up two inches twice -- this is a great way to show you've got selvedge or an interesting-colored caste without making such a scene. Get the trim cuff the same way but only roll from an inch to an inch and a half each time. This works best with narrow jeans and looks more tailored.
It's been a while since short-cropped pants became the hottest trend out there, and it seems just as long that guys have been achieving this look by rolling up longer-cut pants. This cuff is best made by pinching the fabric in the front, flipping up as little as possible, and then twisting the pants about an inch and rolling twice more. Be sure the cuff fits snuggly, you're wearing short dark socks (if any), and that the roll doesn't go too much above your ankle unless you actually plan on digging for clams. Most importantly? Be sure that its not a freezing cold winter day when you decide to wear this outside, lest you look the part of the fashion victim.
An edgy way to show off that hot selvedge is with a thick one-roll cuff--just keep in mind that the thicker the cuff, the more it will chop some inches off your perceived height. Shorter guys should probably stick with a thin one-roll cuff, no more than two inches. Check which length works best for you and then run your fingers around the cuff to smooth it out. To ensure a completely crisp cuff, you can mark where the fold hits and lock it in with an iron and some starch (don't forget to take the jeans off first!).
A one-flip upturn, a double cuff, a thick one-roll, no cuff -- how you treat the bottom of your jeans can say as much about your personal style as the wash, fit, and color. So, have some fun and, most importantly, make sure your cuffs reflect you.