While skinny pants can easily be tucked inside your boots, sometimes that’s not the look you’re going for — or maybe your pants have straight legs and aren’t tight around the ankles, which can make tucking disastrous. Rolling the ends of your pants to wear over the boots is an easy way to make a fashion statement, while not making it look like you’re trying too hard to keep up with the latest trends.
Choose the look you’re going for with your boots. You can roll your pants in several ways, from a very clean and neat roll to a messy roll.
Roll your pants into a 1-inch single cuff and then another to make a double cuff. This will give you a tapered leg and a “messy” roll. You can adjust the height of the cuff according to the boots you’re wearing and your own personal style. You can choose to make the cuffs on both legs the same or make them off a little bit in height and neatness to stay true to a messy look.
Cuff the pants in one single folded cuff at whatever height up the boot you prefer if you’re going for a neater look. Roll the hem up so that the inside seams of the pants show. Generally, if you’re a shorter person, stay away from a large cuff — this will make you look shorter.
References and ResourcesThe New York Times: The Art of the Pants Roll
Complex Style: Style Guide: How to Cuff Your Jeans
Heddels: How to Cuff Your Raw Denim -- The Single, Double, Skinny Cuff