Style FAQ: How to Wear Booties with Jeans

As stylists, we get certain questions from clients and friends over and over again. And one of those questions is, how do I wear ankle boots with jeans? It’s a good question. Style conundrums like this one usually result from trying to rock an in-vogue item that “looks good on everyone else,” but we feel like we just can’t get it right. However! Like high-waisted pants or the mid-calf skirt, some fashion trends present differently on each body type and just need a simple tweak for fit perfection. With a little guidance (our #1 pro tip and 1-2-3 styling options), you, too, can master booties with jeans.

First and foremost, our pro tip for nailing the booties/jeans combo every time: hem your pants to hit right at or above where your ankle boots stop, that way they’re short enough to wear as is and long enough to cuff if desired. If you don’t have a sewing machine at home, many commercial cleaners and alterations professionals offer this inexpensive service to tailor your jeans to the ideal length in relation to your height and shoes. Or if you’re into the fringe hem that’s gained popularly in the past year, cut your jeans to the right length at home. (We recommend using sharp fabric scissors, a ruler, and a fabric marking pencil.)

As we describe three foolproof tricks for wearing booties with jeans, keep in mind that ankle socks, ideally matching or close to the color of your booties, and skinny or straight-leg jeans generally pair best with ankle boots.

1. TUCKED

When tucking your un-cuffed jeans into ankle booties, skinny jeans are pretty much the only way to go. Otherwise, you’ve got a lot of excess fabric and gathering that does not look flattering or streamlined. A classic blue denim wash–and we’re never opposed to moderate distressing–looks great with your typical black or brown leather booties. We also like a monochromatic ensemble, such as black skinny jeans and black booties together, which elongates the appearance of your legs.

2. CUFFED ONCE

Be still our hearts: this may be our very favorite technique for wearing booties with jeans. A single messy cuff of your jeans (about two inches), leaving a sliver of skin between the bottom of the jeans and the top of the booties, is so effortlessly chic. This styling works well with skinny jeans, as the stretchiness of the denim allows you to play with length a bit, gathering fabric at the knees to show a little more skin at the ankles. Achieve a more relaxed look with straight, boyfriend-cut jeans.

3. CUFFED TWICE

This cuff looks a bit different than #2, as the cuff is tighter and more polished. When cuffing your jeans twice, be sure to roll them only the height of the hem (usually between a half to one inch). Because of the tighter cuff, the length of the jeans on your leg will be about the same as the single cuff in #2, with the same sliver of skin between the jeans and the booties. While the double cuff works on all denim washes, you can’t beat a dark skinny jean styled this way, especially when the underside of dark denim is lighter-colored and creates a pleasant contrast.

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