5 Boot Trends to Buy and Skip This Fall, According to Our Editors

Boot season is here, and as a major boot person, that makes this editor particularly excited. As biased as I might be, I stand by the fact that boot season is the best season. Sure, you can point to the layering or the knits as the reason why the fashion just feels stronger this time of year, but I'll be firmly advocating that a solid pair of boots has a lot to do with it.

Curious about which outdated boot styles you should retire to upgrade your wardrobe? Who What Wear's team of editors have thoughts on the matter, so I asked them to name the boot trends they're breaking up with this fall and, of course, which trends you can find them wearing on repeat instead. Let's face it: We'll be wearing our boots nonstop from now until April, so if you haven't found your ideal pair (or two or three pairs) yet, there's no better time than the present.

From the stiletto boots that editors are putting away to the chunky-soled boots that are already trending hard for fall, keep reading to find out which boot trends we're naming as "in" and "out" and then shop each one that made the cut.


Expiring: basic ankle boots

Incoming: second-skin boots

While I'll never truly retire my basic ankle boots, I feel ready to experiment with more directional styles right now. I'm gravitating toward the second-skin knee-high and over-the-knee boots that are on the market.


See the trend:
(Image credit: @rosiehw)

Shop the trend:


Expiring: wader boots

Incoming: chunky knee-high boots

"While over-the-knee boots will always have a special place in my heart, this season I'm skipping them in favor of chunkier, looser to-the-knee styles. Think chunky, leather, and—as the Gia x Pernille Teisbaek pair are aptly named—tubular."


See the trend:
(Image credit: @slipintostyle)

Shop the trend:


Expiring: slouchy boots

Incoming: sleek knee-high boots

"Personally, I'd skip slouchy boots this fall. They may have had some airtime on the runways recently, but I've always found them to be tough to style. Instead, I love how sleek and polished the structured knee-high boots look, and I'll be leaning heavily on the '90s-inspired boots as a staple in my fall and winter wardrobes. I wore this pair from Nordstrom all last winter, and I'm reaching for them again this time around. Chic and super versatile."


See the trend:
(Image credit: @anna__laplaca)

Shop the trend:


Expiring: traditional cowboy boots

Incoming: modern cowboy boots

"I'm surprising myself by saying this, but I think I'm ready to wear Western boots again. It's barely been a couple of years since they were last a thing, but that's fashion for ya. I'm gravitating toward styles that are more chic and polished than literal."


See the trend:
(Image credit: @annadominguez)

Shop the trend:


Expiring: stiletto boots

Incoming: flat boots

"Thanks to COVID, I truly have no interest in stiletto boots right now. I am all about comfort and practicality instead, so I will be buying flat boots that are easy to wear and simple to incorporate into my wardrobe."


See the trend:
(Image credit: @tylynnnguyen)

Shop the trend:

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Associate Director, Special Projects

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.