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As style people (hey there), we’ve experimented with a slew of winter shoe trends over the years to find those ideal silhouettes that are equal parts fashion and function. Sure, we have many of these perfectly acceptable styles at the ready in our closets, but the change in seasons comes hand in hand with our desire for a wardrobe refresh—starting with a winter-boot upgrade.

So with that in mind, we thought we’d share the winter boot trends we’re considering storing away due to their somewhat outdated nature. Alternatively, we’re also sharing the styles we’re excited to test out this season instead. From the 2021 update to wedge boots (yep—they’re back) to platform stompers, keep scrolling to uncover the boots we’re considering in and out 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, platforms boots are the silhouette I can’t get enough of, whether they’re Chelsea styles or chunky knee-highs.”

Phasing out: Block-heeled boots

Wearing: Wedge boots

“Never thought I’d say this, but I think the time has come for the wedge boot to return. I’ve been noticing them more and more lately, and my thoughts were recently 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 it feels more modern. For me, they’re replacing block-heeled boots, which feel just a bit outdated at the moment.”

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.”

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 and since they’re a style that tends to come around again like clockwork, I know they’re a wise investment.

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 look forward to lacing up something a bit cozier by taking the shearling trend for a test drive.”

Phasing out: Pointed boots

Wearing: Chunky Chelsea boots

“I’m still all about the chunky Chelsea boot trend. I’m basically living in them rather than super-pointed booties.”

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.”

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. Thinking about how comfortable I’ll be is enough to convince me.”

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 a Y2K style sky-high platform boots. Is it weird that I’m more scared of walking in those than I am 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.”

Up next, see the fall-meets-winter outfit tricks my East Coast friends swear by.


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