I take it that you’re interested in learning a few ways how to cuff your jeans or pants. In this quick guide, I’ll show you 4 ways that I roll my pants (including my favorite method) that you can copy if you’d like. And then I’ll share how you can cuff your jeans or pants (trousers) with different types of footwear.
First thing’s first, you want to make sure that your pants are either slim or skinny fit. There should be a nice taper down the leg. This will allow for a better looking finish with all four of the methods I’m going to cover. Baggy jeans or pants won’t cut it and will more often than not, look really sloppy.
With that being said, let’s get started.
HOW TO CUFF JEANS OR PANTS FOR MEN
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1. The Double Pants Cuff
The “Double” roll has been my go-to for the longest time. You want to cuff your pants about an inch, more or less, depending on your desired aesthetic.
You simply, cuff it up once and then one more time. It’s a tried and true pants cuffing method that provides an air of casualness to any outfit. Feel free to make it as clean and crisp of a roll as you want, but it doesn’t have to be. I personally like my cuffs to be extra crispy.
2. The Upside Down Pants Cuff
I completely made this one up. I’m not even sure if you can call it a cuff. Instead of rolling on the outside, you roll on the inside. It’s a good way to shorten the length of your pants if you’ve yet to have them hemmed or if you simply refuse to get them tailored.
Make sure that it’s the right type of pants. It probably wouldn’t look right with jeans, but in this case, I thought the wool trousers still looked pretty good after cuffing with the “Upside Down” technique. Try it out and see if it works for you.
3. The Fresh Prince Pants Cuff
Shout out to Big Willy Style for inspiring this next cuffing method. “Chillin’ out maxin’ relaxin’ all cool…” I’m sure you can recite the rest by heart. Either way, you won’t be slackin’ with this cuff. (pun intended)
The “Fresh Prince” is all about casual nonchalance. It’s rolling your pants as if you didn’t care. Just flip them up once and let them be, no fixing or fine-tuning. Effortless, casual, cool—just the way it should be.
4. The Pinroll Pants Cuff
And finally, a favorite among many guys and women—for good reason. The classic “Pinroll” is the most streamlined and sharp of all the cuffing styles. It looks great with sneakers and boots in my opinion. The key is that you have to be wearing tapered pants for it to look good.
The pinroll is best with the tailored aesthetic. I’ll definitely be incorporating the pinroll into my spring and summer getups for sure. I personally like to keep the cuff on the thinner side as it makes for a cleaner finish.
Before we close things out, here are a handful of examples of how to cuff your jeans, slacks / pants / trousers (whatever ya wanna call them!) with different types of footwear from boots and sneakers to loafers.
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How to Cuff Jeans with Boots
When cuffing jeans with boots, there’s only a few things you need to keep in mind. First, the type of jeans matters. Selvedge denim (in the example below) is inherently thicker and a much rougher fabric than that of regular jeans. And so, you ever be pin rolling these bad boys. The upside down cuff would be unwise here as well.
The best course of action when cuffing jeans with boots is to double cuff. Selvedge denim makes for an ultra-clean cuff as you can see above and below. With regular jeans, you can cuff them up any which way you please.
A great pair of dark indigo wash selvedge jeans is from Unbranded.
A Note on Selvedge Denim
You can usually make out a pair of selvedge jeans from the selvedge (self-edge) detail at the bottom of the jean’s cuff. It’s an unmistakable trait of all selvedge denim.
I personally feel that selvedge denim looks better slightly looser with a wider leg opening which these jeans have. These jeans and selvedge denim in general look fantastic paired with rugged work boots.
How to Cuff Khakis or Chinos with Sneakers
Maybe you’re like Dr. Dre and still rockin’ your khakis with a cuff and a crease. With sneakers and chinos, keep it super simple. with a double cuff or pinroll. Make sure that the leg opening is tapered towards the ankle as wide leg trousers or khakis look horrible cuffed up.
How to Cuff Jeans with Loafers
First things first, mind your socks. If your jeans are dark blue, keep your socks darker neutral shade so that they harmoniously blend together. With a pair of casual shoes like penny loafers, keep your cuff slim and trim at no more than 1″. Clean and simple.
How to Cuff Dress Pants (Linen Trousers) with Loafers
And finally, how to cuff your more refined dress pants with casual shoes like a tassel loafer; again (as my college professor always said) K.I.S.S. – Keep it simple, stupid!
A single cuff works well here. With these beige linen trousers (from Alan David NYC), the cuffs were customized into the design and so there’s no uncuffing them.
With dress trousers, keep the cuff clean at 1″ to 1 and a quarter inch. I personally like to have no break with my trousers, which means that the bottom hem of the pants just barely kiss the top of the shoes.
Oh yeah, one more thing, don’t forget the no-show socks with shoes like this.
And there you have it, 4 ways to cuff your jeans or trousers so that you can add a little extra flair to your everyday casual outfits as well as how to cuff your jeans/pants with various types of shoes and boots. I hope you enjoyed this short guide as much as I enjoyed writing it!
What is your go-to method for cuffing your pants?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to seeing you in there.