The Do’s and Don’ts of Cuffing Your Jeans with Ankle Boots

November 12, 2016 Shana Johnson

The first time I wore a pair of jeans with ankle boots, I struggled with the right length and style and cuffing. Now, more than a year after I bought my first pair of ankle boots, I still sometimes struggle with the right cuffing style that works with each style of ankle boot.

Today let’s talk about that last one — probably the most common style of ankle boot. You can wear these with almost any kind of jean or pant — skinny, bootcut, flared, boyfriend, cropped, etc. In my pictures I’m wearing mine with a regular length pair of skinny jeans, but all of the tips can be applied to other styles of jeans as well.

First up, this is probably obvious, but don’t pull your jeans over your boots. Bootcut and flared jeans are an exception, since you want them to come over the boot and be long enough to almost touch the floor. But all other jeans should NOT be pulled over the boot.

Next, with this style of ankle boot, DON’T tuck your pants into your boots. This creates a stumpy look because there is no break in the line of the leg at the ankle. It also makes it look like your jeans are way too long for your leg. So no tucking in for this style of boot.

Ahh, this is better, right?  A simple, imperfect cuff. This is the way I wear them the most often. It’s casual, easy, and is a perfect way to create a little separation between your jeans and your boots. Also, make sure you let your ankle peek out a bit since that little sliver of skin will help visually elongate your leg.

This is a cuffing style that you have to be careful with, since a large cuff like this can shorten the line of your leg. If you have thick or short legs, stay away from this and try a shorter cuff. But if your legs are long and/or thin, this works and is just another fun way to cuff your jeans with ankle boots. Also, make sure your cuff doesn’t go bigger than about 3 inches.

And finally, a rolled cuff. This one is a more casual option that is perfect for your weekend outfits. Leave about an inch of ankle showing in between the jeans and boots don’t roll too much or too little.



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