There’s no article of clothing more universal than a pair of denim jeans. How you wear those jeans, though, well that’s all a matter of personal taste. From the rise of the waist to the fit of the leg and everything in between (button fly versus zipper included), every man’s got his own unique set of denim preferences, like a sartorial fingerprint. Some even prefer their denim shorter. Right now, though, we’re here to talk about one thing, and one thing only: To cuff or not to cuff.
On its face, cuffed jeans shouldn’t require an advanced degree in fashion. And they don’t — all you’re doing is folding back the fabric at the bottom of your jeans, after all. But you’d be surprised at how many people get tripped up by what’s going on at the hem of their favorite denim trousers. And most of the time, it’s only because they didn’t follow a few simple rules.
Cuffed jeans. Stacked jeans. Rolled jeans. Flat-hemmed jeans. These are all viable paths to take so long as you know what you’re doing. That’s where this guide comes in: to show you all your options and teach you how to best go about styling them. So the next time you think about cuffing, rolling, or stacking jeans, you’ll know exactly what to do.
Before we get into styles that require more active styling — cuffed jeans, rolled jeans, stacking jeans, and the like — we thought it best to start off clean with the flat hem. That is, jeans where the denim at the hem has gone unmanipulated. Think of this as the foundation for all your other options; you have to know how to nail this before you can level up.
How to Pull It Off: While it may seem like this is the most low-maintenance way to wear your jeans, you’d be surprised to know that to leave your hem flat, you actually have to put in just as much thought. The difference is that all your thought has to happen before you even pull on your jeans … at a tailor. Get them to hem your jeans so they sit right on top of your shoes, with or without a break, depending on your preference. And have them keep and sew back on the original hem because nothing looks more wrong than jeans hemmed like dress pants.
The single cuff is about as straightforward as you can get. Just take the hem of the jeans and roll it up once so that the underside of the fabric is facing out. Bonus points if you’re wearing selvedge denim — that colored line along the outseam will show off nicely.
How to Pull It Off: Honestly, it doesn’t take much to make a single cuff look good. Feel free to wear single-cuffed jeans with most casual outfits and footwear, like sneakers or chukka boots. Just make sure the cuff isn’t too big or too small. You’re aiming for one to two inches in height, with an inch and a half being your sweet spot.
Take the single cuff, roll the hem one more time — seriously, only one more time or you run the risk of looking like you’re digging for clams — and you’ve got yourself a double roll. Easygoing and classic, it’s a great way to show a little more of your shoes or ankles.
How to Pull It Off: Just like the single roll, you want the cuff to be about 1 to 2 inches tall when all’s said and done. So make sure your first roll is a little smaller. That way the added bulk of the second roll will bring the whole thing up to, and not past, the appropriate height. Speaking of height, you’ll be using a lot of fabric to make the cuff, so you’ll need your jeans to be hemmed a few inches longer than usual to make this work and keep your calves covered.
If you want to add taper to the leg while also cuffing your jeans, look to the pin roll. By adding a vertical fold to the cuffing process, it’ll help make jeans appear slimmer from the knee down. Pin-rolled jeans are also great for highlighting your footwear — so if you’ve got a dope pair of kicks to show off, now’s your chance.
Intrigued? Start by folding over the inseam of the leg vertically to your desired tightness. Then, while holding the vertical fold, roll a single cuff, and then a double, so that it’s nice and secure.
How to Pull It Off: Pin-rolled jeans work best when the pants are already on the slim to straight side. So we wouldn’t try this on any super-wide-legged styles, as they’ll likely balloon out unflatteringly. Otherwise, effectively the same rules apply as the double cuff.
Just like the name implies, this is one really, really big cuff. Specifically, we’re talking about a single cuff greater than four inches in height. Generally reserved for bigtime denim heads and Japanese workwear aficionados, the oversized cuff traces its roots back to when men had to cuff their jeans this high for a reason. These days, it’s one of the toughest cuffs to rock.
How to Pull It Off: In the interest of showing you all your options, we’re going to keep this one on the list. But be warned, the oversized cuff requires more know-how to pull off than we can teach you in a single guide. And even then, it just doesn’t work for a lot of people; if you’re in any way vertically challenged or self-identify as “stocky,” we’d steer away. If you really want to go for it, though, here are a few tips: Opt for a heavy, raw denim that can stay up on its own. Try jeans with a looser, more boxy fit. And pair it with other heritage staples like Converse high-tops, Red Wing boots, and anything with military-style leanings.
Unlike cuffed jeans, stacking jeans doesn’t require you to fold your jeans in any way. In fact, just the opposite: Stacking jeans is all about leaving enough extra length at the bottom of your pants that they break a number of times — or stack — on top of your shoes. Once a sign of ill-fitting clothing, stacked jeans these days make it clear that you’re trend-forward in the way you dress. Which is definitely not a bad thing.
How to Pull It Off: The key to stacking jeans is appearing intentional, so stick to skinny jeans. And we mean skinny. Anything looser than that will make you look like a slacker, or worse yet that you have no idea what you’re doing. Stacked jeans will also draw attention to your footwear. You can go one of two ways with that. You can go for a clean and simple pair of premium white sneakers or suede Chelseas. Or you can go for something bulkier like a work boot. The ball’s really in your court — just wear your kicks with confidence and you’ll be all set.
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