These 10 Winter Boot Trends Are Starting to Feel Dated, so We're Replacing Them


(Image credit: Jade Belmes)

Over the past few months, we've made predictions based on the fall trends we'd want to wear and planned out the outfit combinations we'd be trying. But now that we're well acquainted with our cold-weather wardrobes, we have to admit that, well, we've been playing favorites. Of all the boot trends on deck this season, each of our editors has cherry-picked the styles that speak to them the most and have been prioritizing those top picks. The change in seasons comes hand in hand with our desire for a wardrobe refresh—starting with a winter-boot upgrade.

To find out what we'll actually be wearing throughout the winter, we discussed the winter boot trends we're phasing out due to their somewhat outdated nature. Delicate and tall-heeled boots aren't making the cut this season for these editors, but instead, many of us are leaning toward chunkier utilitarian styles this season. Keep scrolling to uncover the boots—from the 2021 update to wedge boots (yep, they're back) to platform stompers—we're considering to inspire your next winter shopping haul.


Phasing Out: Slouchy Boots

Wearing: Platform Boots

"Right now, I'm pressing pause on slouchy boots in favor of more structured styles. In particular, platform boots are the silhouette I can't get enough of, whether they're Chelsea styles or chunky knee-high boots."


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(Image credit: @SLIPINTOSTYLE)

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Phasing Out: Block-Heeled Boots

Wearing: Wedge Boots

"I never thought I'd say this, but I think the time has come for wedge boots to return. I've been noticing them more and more lately, and my thoughts were confirmed when I spotted Amina Muaddi in a pair on Instagram. The key is to go for wedge boots with a pointed toe and a slimmed-down silhouette. That way, they feel more modern. For me, they're replacing block-heeled boots, which feel just a bit outdated at the moment."


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(Image credit: @AMINAMUADDI)

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Phasing Out: Tall-Heeled Boots

Wearing: Flat Boots

"I'm personally not wearing high-heeled boots these days because the pandemic has fully converted me into a comfort-first dresser. I much prefer flat boots like these very cute ones from our Who What Wear collection. They'll truly go with everything and are so easy to walk in for long periods of time."


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(Image credit: @basicstouch)

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Phasing Out: Croc-Effect Boots

Wearing: Sleek Western-Inspired Boots

"The croc-effect craze definitely took hold of my wardrobe, and while I'm not mad at it, I'm ready for something new. I'm excited to see that Western-inspired boots are making such a big comeback right now because they add an undeniably cool element to just about any outfit. Since they're a style that tends to come around again like clockwork, I know they're a wise investment."


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(Image credit: Jade Belmes)

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Phasing Out: Embellished Boots

Wearing: Utilitarian Boots

"I love pretty shoes—the more over-the-top the better. But when it comes to boots, I choose function over form. I'm excited to bring my trusty patent-leather Dr. Martens back into the regular rotation, and I look forward to lacing up something a bit cozier by taking the shearling trend for a test-drive."


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Phasing Out: Pointed Boots

Wearing: Chunky Chelsea Boots

"I'm still all about chunky Chelsea boots. I'm basically living in them rather than super-pointed booties."


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Phasing Out: Animal-Print Boots

Wearing: Classic Riding Boots

"I'm sure I'll be into them again at some point, but for now, I'm taking an extended break from animal-print boots. They don't feel quite as fresh as other styles this season. Instead, I've been gravitating toward classic riding boots. This Reformation pair, in particular, has been on constant rotation. They make everything look so much chicer and more polished."


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Phasing Out: Delicate Boots

Wearing: Chunky Boots

"I own a lot of delicate boots (think suede, kitten heels, or embellished), yet lately, I've only wanted to wear my chunkier, more utilitarian-inspired styles. It works out because they tend to be more comfortable anyways."


Phasing Out: Stiletto Boots

Wearing: Chunky Boots

"I'm finally giving in to the chunky-boot trend after a year of clutching onto my sleek stilettos. When I first saw this style on the Bottega Veneta runway, I never thought I'd go there, but now, I can't stop dreaming about them. Just thinking about how comfortable I'll be is enough to convince me."


How to wear them:
(Image credit: Jade Belmes)

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Phasing Out: Thigh-High Platform Boots

Wearing: Pencil-Heeled Boots

"I've been wearing thin-heeled boots more than I thought I ever would. I personally like to opt for a pencil heel when I'm looking for a more dressed-up outfit—it makes everything look much more elevated. A boot style I'm not wearing is Y2K-style sky-high platform boots. Is it weird that I'm more scared of walking in those than stilettos? I think many people pull them off so well, but I'll be passing on those, as I don't think they mesh with my personal style."


How to wear them:
(Image credit: @thatgirlyusra)

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Up next, See the Fall-Meets-Winter Outfit Tricks My East Coast Friends Swear By

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.