Cuffing 101

The Modern Otter | Timberland

It sounds simple, but the ins and out of rolling your pants can be complicated.

Did you know the size of the cuff should be proportional to your height? And showing a bit of ankle can give you the appearance of being taller?

And what about a pinroll? That’s like, advanced cuffing.

Let’s break it down because denim cuffs are a little different than chino cuffs. 


With denim, the seam on the pant is small, so you can basically do whatever cuff size you want. 

Jeans need at least one cuff 

The Modern Otter | Timberland

For this first look, I cuffed my Timberland selvedge denim over waterproof oxfords. I rolled the hem twice, but the general rule with selvedge denim is always cuff it at least once. 

The Modern Otter | Timberland

Selvedge denim is distinguished by the red or blue stitching on the outside seam of the jeans, so that’s really what you’re showing off.

Hide your ankles

Yes, I am wearing socks! But I stick to no-show socks anytime I’m showing ankle.


For the second look, I went with a bold cuff. This one isn’t for the style-shy. It’s about 6-8” high but it’s definitely a growing trend. Denim is too thick to cuff 3+ times without looking bulky, so instead you do one giant cuff. 

The Modern Otter | Timberland
The Modern Otter | Timberland
The Modern Otter | Timberland
The Modern Otter | Timberland
The Modern Otter | Timberland

You see it a lot in Japan with denim aficionados and it’s almost always with a more relaxed, straight leg or classic fit denim. The loose fit of the pant is balanced out by the bold size of the cuff. It’s a great way to show your entire boot, which is usually lost under long pants.

But beware: this style looks best on tall guys! The larger your cuff, the shorter you look. It segments the line of your leg.

But if you’re feeling bold, the higher the better!


The Modern Otter | Timberland

Rolling a chino adds style to a look. It creates a visual stopping point, just like a shirt collar or a sleeve cuff at your wrist. I tend to roll my chinos once or twice. It makes for a more polished, clean look, especially when paired with my Timberland boots.

With chinos, the hem of the pant usually dictates the width of the cuff

There’s an extra 1” to 1 3/4” of fabric stitched into the bottom, so if you roll it exactly at the seam, you’re golden.

Adjust the cuff to your height

If you’re under 5’10” stick to cuffs that are 1 1/2” or less. If you’re over 5’10”, stick to a 1 1/3” cuff. The size of a cuff can actually change how tall you appear.

It sounds crazy, but it’s true.

In the summer I roll my cuff twice to show some ankle (which is a great trick if you’re on the shorter side. A narrow cuff rolled two or three times with a little skin showing will make you look taller).

When in doubt...

Roll all your pants once or twice with a 1.5” cuff. It works with everything and always looks sharp.

P.S. A pinroll is when you pinch the fabric on your pant leg and fold it flat against your leg before you cuff it, essentially creating a pleat for your pant. A great option with oxfords or loafers but stay away from sneakers unless you want to look like you’re wearing ‘dad jeans’.

*This post was sponsored by Timberland, but all thoughts, opinions, styling decisions and life choices are my own. As always. ;)

StyleAaron Wester