Skip the Flats—Cindy Crawford's L.A. Denim Trend Looks Better With Heels

By Kevin Harson10 October 2025

The celebrity-approved way to wear flare jeans isn't grounded, it's elevated. And no one demonstrates this better than the OG supermodel, Cindy Crawford. The 5'10" style star is constantly spotted in the long, leg-lengthening denim silhouette, and here's the kicker: she almost exclusively pairs them with a heel.

Crawford often leans into the elevated aesthetic by opting for sleek black pumps, pointed-toe heeled boots, or even sophisticated high-heeled sandals, depending on the occasion. The flare of the jeans, when combined with a little extra height, elongates the leg, ensuring the outfit says, "I'm off the clock, but I still have a reservation."

So, take a page from the ’90s icon's playbook and leave the flats for your leggings. Whether you choose a dark-wash wide-leg or a true '70s-style flare, the key to unlocking its full potential is shoes with a couple of extra inches. Find a classic stacked pump or a sleek leather bootie that peeks out under the hem, and you'll find your new favorite, most flattering denim outfit formula. Keep scrolling to browse jeans, shoes, shirts, and accessories that can be mixed and matched to re-create Crawford's look for yourself.