Lots of readers/viewers have been asking me to do an article and video about how to roll or cuff men’s pants, so I’m finally doing it! The article is great and all, but the act of rolling your pants is not something easily shown in still images, so do yourself a favor and watch the video below for the fully experience.
 
With the exception of jeans and boots, you should only be rolling your pants in the spring and summer, unless you’re in a climate where it’s warm all year-round. This is very much a warm weather flair to add to your dark wash jeans, chinos or khakis or even wool pants and trousers. But it is a little odd to wear during the colder, winter months.

How To Quickly Measure Cuff Width

Before we begin, let me show you a quick and dirty way to figure out the proper width of your cuff by using your finger joints. The each joint of your index finger is roughly an inch long.

So if you need the cuff width to be about 2″ wide, the top of the cuff would hit right around the second or middle joint, like in the picture below:

The Simple Cuff

This cuff works especially well with slim fit jeans. I like to use this cuff when I’m going for a cleaner, sleeker look with a client. I’d caution against using it with chinos or other pants, as the fabric can be a little floppy around the ankles.

You also want to avoid using this cuff if you’re wearing straight fit jeans because your ankles will be swimming in a bunch of fabric. Use the pinroll cuff in the next section, instead.

Before you start cuffing, you should already have your jeans and shoes on. Otherwise, it’s harder to tell what the finished product looks like and if you’re showing the right amount of ankle. Hopefully you’ve already seen my men’s jeans fit guide so you know that your slim fit jeans should have a slight break at the hem. This cuff won’t look right with any other type of pant break.

How to Cuff

Low Top Shoes

If you’re wearing low top shoes, roll up your jeans’ cuff once.
The cuff width should be between 1.5” to 2”. If you’re on the shorter side, get the cuff as close to 1.5″ as possible. If you’re on the taller side, go for 2″. This will maintain the proper promotions for your body type.

Make sure that the roll is the same width or thickness on the front and back of the pants before you do the second roll. After finishing the second roll, the bottom of the cuff should just hit the top of your outer or inner ankle bone, like in the image below:

Boots or High Top Shoes

It’s the same as low tops: do at least 2 rolls and make sure to maintain the 1.5″ to 2″ cuff width, depending on your height.

The bottom of the cuff should either lightly graze the top of the shoe or boot or go a little bit past the top of the boot or high top. The image below, has the pants rolled up 3 times on the left and 2 times on the right. Both are equally acceptable lengths. I prefer 2 rolls, as 3 makes it look a little too military for my tastes, but 3 is just fine if that’s what you prefer.

The Pinroll Cuff

This cuff is great for any cut of jeans, as well as chinos. I like this roll because it eliminates the issue of your pants swimming around your ankles when they’re cuffed.

Again, start with your pants and shoes already on. Check my men’s jeans fit guide and chino pant fit guide for details about the type of break your pants should have before cuffing. If your pants aren’t fitting properly or they’re too long at the hem, the roll will look big and chunky around your ankle, which you don’t want.

How to Cuff

Low Top & High Top Shoes and Boots

To start, pinch the fabric on the inside of your ankle so it feels slightly snug against your leg or ankle.

Now fold the fabric over towards your heel. The reason why we do this is because it hides the fold better than if you folded the fabric towards the front.

With your thumb still holding the fold against your ankle, start rolling the cuff up with both hands. Make sure the roll is between 1 to 2 inches wide. If you’re on the shorter side, keep it around 1″ and go closer to 2″ wide if you’re taller. This will maintain the proper proportions for your stature.

Now roll up the cuff a second time. You want to roll at least twice to make sure that excess fabric that we folded over won’t come undone. It won’t stay with just one roll.

if you’re wearing low tops, you want the bottom of the cuff to hit around 1.5 to 2” above your outer ankle bone, like the image below. If you need to roll 3 times to get there, do that.

The only exception to the 3 roll maximum is if you’re wearing boots or high tops. Then you need the cuff to just cover the top of your boot or lightly graze the top of your high tops when standing up. The image below has the cuffs rolled twice.

That’s it! Now cuff all the things!