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Boot season is almost 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 to 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Curious about which outdated boot styles you should retire to upgrade your wardrobe?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 especially gravitating toward the second-skin knee-high and over-the-knee boots that are on the market.

Expiring: over-the-knee 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 pair are aptly named—tubular.”

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 structured knee-highs 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.”

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.”

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.”

Next, the new fashion finds I’m obsessing over right now.

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