It's often the simplest problems that are the trickiest to navigate when it comes to getting dressed. A perfect case in point of this is figuring out just what to do with the bottoms of your jeans. Rolling, cuffing, tailoring, and stacking are all easy maneuvers to get the job done—in theory. But executing style moves is often easier said than done. Truth is, just as in 2016 there are more options for what kind of pants to wear, there are also more decisions to make today in terms of finessing the hem of your jeans the right way. Here, we've laid out everything you'd ever need to know about navigating the new, ultra-diverse climate of cuffing.

The Double Roll
The degree of difficulty in double roll is 1-5. It looks with pretty much everything, but particularly with low-top sneakers and dress shoes.

How to do it: This is the kind of cuff most guys think of when they're talking about cuffing their jeans. We call it the double roll because you never should roll them up more than twice. If you're an average height guy wearing a 34" inseam jean, rolling them up four of five times will make you look like you're wearing ankle weights. The key to the double roll is going for a 1.5" cuff. The key there is making the first roll less than an inch and the second one just a touch bigger. Once you've rolled, spend a few seconds messing with them. Push one side down a touch on each leg and tweak until you've reach a healthy, elegant level of "whatever" attitude. After all, these are jeans—not suit trousers.


The Deep Cuff
The degree of difficulty is 5 and it looks best with Work Boots, Old School High-Tops, etc.

How to do it: [/i]The reason the oversized single cuff clocks are our most difficult is because it simply doesn't look good on most guys. Though this style lines the pages of Japanese magazines like Free & Easy, it channels a level of commitment to old school work wear most guys aren't comfortable achieving in this age and time. In other words, because it comes from the days when hard-working men cuffed their jeans out of necessity, not style, it looks best when worn alongside things like Red Wing boots, PF Flyers, denim shirts, chore jackets, and U.S. Navy-inspired beanies. (An oversized cuff would just look silly with some Yeezys.) Also, if you're shorter than six feet tall or refuse to skip leg day, adding a four-or-five inch cuff to your jeans won't do your stockiness any favors.

The Stack
The degree of difficulty in this is about 4 and it looks best with hyped-up running sneakers, timberland-style boots, and rock star boots
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How to do it: Stacking one's jeans used to be perceived as sign of laziness, or at worst, a lack of style. But over the past few years, a slim stacked jean has become an insider's shorthand for of-the-moment cool guy style. Now, a stack still only works with uber-slim denim, so if that's not your speed it's best to leave this to those who embrace a pencil-thin leg. Stacking can work with a minimalist pair of kicks like Common Projects, but it's best suited for sneakers with a built-in sock-like upper (think Yeezys, Flyknits, etc.). A new-wave hip-hop move is to pair them with a pair of box-fresh Timbs, while thanks to high-end rock star-inspired brands like Saint Laurent, the skinny stacked jean has become as much a part of of the look as some slim-profile suede boots.

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