Here's How Everyone Will Wear Ankle Boot Outfits This Fall

last updated 10 August 2023

Welcome to our Ask an Editor series, where each month, I’ll answer questions submitted by our lovely readers. How does it work, you ask? At the end of this story, submit your style- or fashion-related questions, and I’ll pick the top submission to solve next month. (And maybe even give you a shout-out!)

With ankle boots winning as the number one shoe style for fall, it’s no wonder our readers are looking for fresh ways to wear the classic boots. This month, I’ve received several requests asking for ankle boot outfit inspiration, so to ensure our dear readers are set with plenty of ideas, I’m sharing my go-to combinations for fall. Each look is timeless, so you can wear it on repeat season after season. From a simple jeans-and–belted outerwear look to a matching blazer outfit that could work for the office, bookmark (and try!) each combination the next time you reach for your ankle boots.

Scroll down to check out seven ankle boot outfits that will never go out of style.

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Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.