The Definitive Guide to Cuffing, Rolling, and Stacking Your Jeans

How to roll, hem, or even cut a pair of jeans to make sure

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

Degree of Difficultly (1-5): 1

Looks Best 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

Degree of Difficulty: 5

Looks Best With: Work Boots, Old School High-Tops.

How To Do It: The reason the oversized single cuff clocks in as 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 workwear most guys aren't comfortable achieving in 2016. 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

Degree of Difficulty: 4

Looks Best With: Hyped-Up Running Sneakers, Timberland-Style Boots, Rock Star Boots.

How To Do It: Stacking one's jeans used 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.

The Cropped Hem

Degree of Difficulty: 2

Looks Best With: High-Top Sneakers, Chelsea Boots.

How To Do It: All you have to do here is take the jeans to your tailor while wearing your favorite high-top footwear, like Chuck Taylors or some crepe-soled Chelsea boots. Just know that because they're extra cropped, they're basically only suited for particular shoes in your rotation. (But seeing as its 2016, it's okay to have pairs of jeans suited for particular occasions.) The point of the cropped hem is to make your shoes the star of the show, so hem them so your jeans just barely graze the tops of your sneakers. Ask for "no break" and any good tailor will know what to do. And for shorter guys, a cropped hem is the easiest way to make your legs at least look like they're longer and leaner than usual.

The Cutoff

Degree Of Difficulty: 3

How To Do It: Though it seems easy to take a pair of scissors to your favorite jeans, it doesn't happen well without some finesse and patience. After you bust out the chalk and scissors, make sure to cut the jeans to a height that gets them to a slightly cropped height (if not quite as high the above cropped hem). The benefit of the cutoff jeans is that it works with any width jeans you prefer from uber-skinny to wide leg, and is a subtle way to add character to a classic outfit. If you're opting for a wider leg jean, you may want to cut them slightly higher to just above your ankle. (Lean into the swerve, you know?) But where the difficultly comes from is achieving a frayed edge that looks a little disheveled without being sloppy. Just keep in mind this works best for washed or worn-in jeans (a frayed edge on some fresh raw selvedge looks out of place). Know that by cutting off a pair of jeans you're essentially putting them on the clock. They usually cross over into sloppy after about a year.

Up Next: How to Roll Your Pants

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