The “How to Wear Booties With Jeans” commandments should be as simple as owning both booties and jeans and wearing them together—but they’re not. Some bootie styles objectively look best with an ankle-length distressed hem; others are only meant to be seen poking out from beneath a flowing pair of wide-leg jeans. Then there are the sturdy black booties that can be worn with any pair of jeans. Those provide infinite options to the booties and jeans expert, but paralyzing choices for a newbie.
All that said, figuring out how to wear booties with jeans is the most easily solvable style rut out there. The reason? Jeans and booties are the most popular celebrity outfit duo since the 2000’s Juicy tracksuit and Uggs. After poring over all the ways celebrities have paired booties with jeans, we’ve honed in on six fail-safe ways to wear them. So if you’ve ever stared down a pair of red suede ankle boots and frozen, unsure which jeans to pair the statement boots with, don’t stress: The following six outfits are for you.
Booties that fall on the taller side shouldn’t be hidden under a dress or baggy jeans. If you own a pair of slouchy booties, tuck your jeans into the tops of your booties to let those shoes shine. Emily Ratajkowski wore her white booties with straight leg jeans, creating a fold-on-fold look where denim meets leather.
Tan suede booties are the backbone of winter wardrobe basics. Why not build your booties and jeans outfit around them? Pair a tan bootie that hits right at your ankle with 7/8-length jeans in a medium wash. The rest of the pieces are up to you as long as they fall in the camel or tan family—but if you’re wearing a bulky top, make sure you give it a French tuck. There you have it: A jeans and booties outfit that’ll stay in style for years to come, like Cindy Crawford‘s.
Pop of Color
If you’re wondering how to wear booties with jeans when your booties are an impractical color—deep purple, fuchsia, you name it— you’ve come to the right place. When your booties are a bright color, let them be the statement portion of your outfit—that is, don’t hide them by making your whole look the same color. Hilary Duff‘s suede pink booties pop against her tried-and-true skinny jeans because they’re the only pink part of her look (and because they’re not hidden under a long denim style).
Levi’s 501s are an eternal celebrity favorite. When you’re choosing a bootie to wear with them, you need a style with the denim’s same vintage flair. Kendall Jenner has the right idea with her black, block heel booties. Tuck them under a straight-leg jean and finish with a cropped jacket, and you’ve got legs for days.
From a practical perspective, stiletto booties like Lea Michele‘s keep wide-leg or frayed denim from dragging on the ground. From a style perspective, a thin stiletto bootie heel contrasts perfectly with a flowy jean. We’re in an age of more-is-more fashion, so top off wide-leg denim with a slouchy turtleneck and oversized coat.
Ladies who aren’t fans of heels, we’ve got you. Motorcycle booties are still a celebrity favorite—just see Brie Larson‘s off-duty outfit. Motorcycle boots belong with a skinny jean that hits above the ankle; between the rounded sole and the bulky straps, these booties aren’t meant to be draped with excess denim.