How to Roll Up Your Jeans: 3 Stylish Ways

Rolling your jeans can make them even more versatile and stylish. If you like to wear your pants a little longer or if you don’t want to deal with getting them hemmed, you can always rely on rolling your denim up. People have been making their bottoms more adaptable by rolling and cuffing them since pants were first invented. It’s the original functional fashion.

There are a few ways to roll your jeans properly. This guide will help keep you looking good in your pants while you’re out there adventuring.

The 3 Ways to Roll Up Your Jeans

The Double Roll
The Thick Roll (Cuff)
The Pinroll (Tapered Roll)

The Double Roll

Best with: Skinny Jeans
Hard with: Baggy Jeans

This classic method of rolling your jeans helps you keep your favourite pair of jeans versatile. When you’ve got things to do (and want to look good doing them) this is your best and most stylish option.

To get a sharp-looking double roll, follow these three steps:

  1. Take the bottom of your jeans and flip them up, creating an overlap of about an inch or less.
  2. Roll the hem a second time, making the second roll slightly wider than the first.
  3. Smooth out the roll and make sure it’s an even width front-to-back and and even height on each leg.

    This look is great with hi-rise, low-rise, and slender shoes like your Chuck Taylors. It’s most easily done with lightweight fabrics.

    How to Wear the Double Roll: Footwear Considerations

    Make sure you’ve got the look right by rolling up your jeans to the right height, based on your footwear:

    • Boots and high-tops: The bottom of the roll should hit just above the top of the shoe.
    • Low-top shoes: The bottom of the roll should just hit somewhere between the top of your ankle bone and 1.5” above your ankle bone.

    The Thick Roll (Cuff)

    Best with: Selvedge Jeans
    Hard with: Wide-leg Jeans

    This look is from the days when working-class folks cuffed their jeans out of necessity. It looks great with Chelsea boots or casual sneakers, plaid, and a relaxed attitude. It’s also a clever way to show off the quality of your apparel, with a colourful selvedge seam.

    To nail the thick roll with your jeans, follow these 3 steps:

    1. Start with a well-sized pair of jeans and fold the bottom up over itself.
    2. Adjust the overlap to about 2” for women and up to 3 inches for men.
    3. Make sure each leg is even and head out on an adventure.

    Check out this look on our Men's All-Weather Denim Slim.

    How To Wear the Thick Roll: Footwear Considerations

    Embrace the roots of this roll and pair it with a structured boot or high-top. For the best look, make sure the bottom of the roll hits just above the top of your shoe.

    The Pinroll (Tapered Roll)

    Best with:Lightweight, Loose Jeans
    Hard with: Skinny Jeans

    Have a favourite pair of jeans that are loose-fitting at the ankle? You can transform any pair of relaxed jeans into joggers with this roll. Whether you want fabric out of the way for a bike ride, or you’re trying to keep the hem dry on a rainy day, this pin roll is a crafty trick.

    Here’s how to roll jeans with a tapered pin roll, just follow these 4 steps:

    1. Pinch the fabric on the inside of your ankle so that it’s snug leg.
    2. Fold the denim over, towards your heel.
    3. With your thumb holding the fold against your leg, use both hands to roll jeans up over themselves. Make sure the first roll is 1-2 inches wide.
    4. Roll the pants over one to two more times to make sure fold doesn't easily come undone.

    The tapered roll is great for almost any type of jean, except for those that are already pretty tight at your ankle. It’s most easily done with lightweight or well-worn jeans that have some flexibility but that will still hold the tapering fold.

    How To Wear the Tapered (Pin) Roll: Footwear Considerations

    The height of this roll is similar to the Double Roll.

    • Boots and high-tops: The roll should hit just at the top of your shoes when standing.
    • Low-top shoes:The bottom of your jeans should hit around 1.5” to 2” above your ankle bone.

    How Long Should Your Jeans Be?

    Before you roll your denim, they should be long enough to skim the tops of your shoes. None of these stylish rolling methods will look quite right if you’re starting off with jeans that are way too long or short.

    If you want a quality, versatile pair of jeans to practice your new rolling knowledge on, you’re in luck. Check out our selection of functionally fashionable Women’s Jeans and Men’s Jeans now.