The Dos and Donts of Cuffing Your Jeans with Ankle Boots

We’re going to talk about a different style of ankle boot — the lace-up bootie. These are generally a lower height than other ankle boots, hitting right at or below the ankle bone at the top of the foot. These are easier to wear with a lot of things because they don’t cover up your ankle and make your legs look wider. But there are still some wrong ways to wear your jeans with them…

First up, don’t wear them un-cuffed if your jeans are regular or long length. The reason you can wear your jeans un-cuffed with regular shoes is because the front of your foot shows in most other shoes, so the leg is elongated and breaking up that long line is generally bad. But when your entire foot is covered, there needs to be some skin showing or else your foot can look blocky and your legs can look stumpy. So those ankles need to show! If your jeans are cropped or ankle-length, then you’re okay. But a little tiny sliver of skin or no skin at all is not flattering. We want to see part of your leg, which will break up the space between the jeans and the bootie, avoiding stumpy looking legs.

One little cuff is the way I wear them the most often just because it gives off a casual and easy-going vibe. The lighter section of denim provides a good bit of contrast at the hem, breaking up the shoes and jeans and showing off those thin ankles!

Another way to cuff is with a double (or triple) cuff. Be careful your cuff doesn’t get too thick, since that can create a big band around your ankles that will make them look wide. But the point of the double cuff is to show off a little more ankle, which is even more flattering.

However, based on your length of jeans, even a double cuff is sometimes not enough. The photo below shoes a double cuff that is very low down and close to the bootie, so make sure that you cuff it enough to show that ankle! The problem here also is that it’s obvious that it’s a double cuff, but since it’s so low to the shoe, it looks like your jeans are too long or your legs are just really short. In your mind, a double cuff would obviously make your jeans much shorter than normal, so a double cuff so down low plays with your eyes and gives the illusion of shorter legs. No good.

If your jeans are extra long and you’re afraid of rolling the jeans too many times and creating too thick of a band, try one really tall cuff, like this one. This style certainly doesn’t work with all ankle boots — in fact, it doesn’t work with most ankle boots. But here it works as long as your cuff makes your jeans high enough to create at least a 2-inch wide gap to show off those ankles.

Are you getting the hang of it? We still have two more boot styles to go, so if I haven’t gotten to your favorite style of boot, don’t fear! Good luck, and happy cuffing!