Winning Formula: The Outfit Cindy Crawford Keeps In Rotation

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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.

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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).

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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.

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In NYC, 2017

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With husband Rande Gerber in Paris, 2017

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In NYC, 2015

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At Heathrow Airport in London, 1992