Winning Formula: The Outfit Cindy Crawford Keeps In Rotation

Full-profiled Cindy Crawford posing for a photo

As much as we like to experiment with trends, there’s something about leaning on basics that feels refreshing now and again. From white T-shirts to denim, having a simple formula on standby is ideal for those laid-back moments like running errands, traveling or low-key hangs with friends or a significant other. The goal when going casual is to always maintain polish, and that’s where Cindy Crawford comes in. The style icon is a pro when it comes to off duty-chic (she is a supermodel after all), regularly leaning on a leather jacket and jeans as her uniform du jour. (And by regularly, we mean consistently since the ‘90s!)

From vintage-style straight legs to black skinnies and flared fits, Crawford mixes up her denim look but sticks to a slick moto-style leather jacket to top off her go-to ensemble—a versatile outfit to put in rotation this fall no matter your silhouette preference. With a simple tee and ankle boots, it’s incredibly effortless on easy days. When you want to kick it up a notch (and we know you will), take a cue from Crawford and swap in a festive top and heels—a perfect combination for drinks, date night or a fun work event.

Since you’re always in need of an outfit you can throw on in seconds flat, ahead, we’re decoding Crawford’s signature jeans-and-leather-jacket formula as she’s worn it through the decades. Then, shop the pieces you’ll need to embody the model’s casual-cool aesthetic with modern flair. It’s a winner.


Dressed Down

For a relaxed look, Crawford goes for a sleek leather moto jacket and rotates between straight-leg jeans and skinnies in both light and dark washes. As for the extras, everything from crewneck tees to a drawstring hoodie and fitted turtleneck are her go-tos up top, while a sleek ankle boot, sneaker or flat can work as the finishing touch in footwear (a square-toe silhouette is quintessential Crawford in the '90s).


Dressed Up

After hours, Crawford keeps the sleek moto and often reaches for darker washes, black skinnies or leather-effect jeans. For fashion-girl flair (because, duh, she’s a supermodel) glamorous tops and classic-with-a-twist heels (typically pumps or strappy sandals) are her signatures.


In NYC, 2017


With husband Rande Gerber in Paris, 2017

Getty Images

In NYC, 2015


At Heathrow Airport in London, 1992