6 Ways to Wear Fall Boots Like Cindy Crawford, Nicole Kidman, and More

Are you ready? It's almost time to retire your summer sandals and bring those fall boots out of storage. Gone will be the days of worrying about the perfect pedicure—instead, you'll be worrying about staying warm in crisp fall weather without sacrificing style. Well, it just so happens that celebrities are experts when it comes to this. Below, I've rounded up outfit ideas to wear with three different types of fall boots, and you might want to start taking notes.
Ashley Graham, for instance, is a proponent of over-the-knee boots, which she recently teamed with an oversize denim jacket worn as a dress. Ever the sophisticated dresser, Nicole Kidman wore the ultimate office-appropriate outfit with boots, including a sleek blazer and flared jeans. Cindy Crawford went for a model-off-duty look with a leather jacket and knee-high suede boots—a very cool combo if you ask us.
Scroll down to see how these celebs, plus Rihanna, Gigi Hadid, and Kaia Gerber, wear boots with jeans and shop their looks.
Heeled Boots
On Nicole Kidman: Ray-Ban sunglasses; Celine bag
On Cindy Crawford: Gucci bag
On Rihanna: Palace Skateboards sweatshirt and sweatpants; Off-White boots
Flat Boots
On Gigi Hadid: Boys Lie Play, Boy Cami ($35); Dr. Martens 1460 W Boots ($140); Missoma Gold Axiom Chain ($214); Bvlgari x Alexander Wang Serpenti Bag (available to preorder September 9 and purchase September 23)
On Kaia Gerber: Prada hat; Alexander Wang Leather-Trimmed Houndstooth Wool Blazer ($1395)
Over-the-Knee Boots
On Ashley Graham: Fendi S/S 19 Baguette
Next, I'm 5'10" and these are the trends I will and won't wear.

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.
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