8 Boot Trends That Are Hitting Their Expiration Date This Fall

Now that we can feel the air getting crisper and the weather getting cooler, we’ve officially entered boot season. As biased as I might be (I am a November baby, after all), I stand by the fact that boot season is the best season. For one, the outfits are just better. 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.

Great, now that we’ve got that settled, let’s get into what you’re really here for: boot trends. Curious about which outdated boot styles you should retire to upgrade your wardrobe? I asked Who What Wear editors 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 sock boots that multiple 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 we’re here for.

Expiring: Basic round-toe boots. Incoming: Square-toe kitten-heel boots. “Everyone’s idea of basic, everyday boots with a rounded toe and block heel has been replaced by versions with squared toes and kitten heels. They’re as comfortable and walkable as their round-toe counterparts but more interesting and special.”

Expiring: Sock Boots. Incoming: Wide-shaft boots. While the look of a pair of boots clinging to your ankle was once something to strive for, sock boots have been on the decline for a few seasons now and I can confidently say they’re “expiring” this fall. As for what’s replacing them, boots with a wide shaft, aka the area around your ankle and calf. The roomier look that labels like Staud and Dear Frances are pioneering feels polished, sophisticated, and ultimately timeless.

Expiring: Basic ankle boots. Incoming: Chunky boots. “Right now, my basic ankle boots are getting pushed to the back of my closet. In their place are chunky styles that were all over the F/W 20 runways and are set to take over this fall. I especially love the modern takes on Chelsea boots which are finished with a high leg.”

Expiring: Platform boots. Incoming: Rubber wellies. “While they aren’t completely ‘out’ platform boots don’t seem as thrilling and fresh as they did last season. Instead, I’m finding myself really intrigued by the wellington rubber boots that have been trending this season. Fashion girls have proven these shoes are way more versatile than you might think!”

Expiring: Heeled boots. Incoming: Kitten heels and platform boots. “As much as I live for a heeled-boot moment, this fall I’m going to be giving my ankles a break and not opting for anything above 4.5 inches. Instead, I’ll be opting for kitten heels at their highest this fall, and at their lowest, platform boots so I can still get the feeling of being taller without the blister to match.”

Expiring: Sock boots. Incoming: Chunky, lug-sole boots. “While there are still some fresh silhouettes out there, I think many sock-boot styles will be replaced by chunkier, lug-sole boots this season.”

Expiring: Over-the-knee boots. Incoming: Flat riding boots. “My extra-high knee-high and ankle boots are not getting a lot of action this season. Instead, I’m gravitating towards flat, equestrian-style riding boots—a trend we saw all over the runways.”

Expiring: Heeled boots. Incoming: Flat lace-up boots. “I can’t imagine wearing heeled boots at all during the pandemic, so I’m replacing them with flat lace-up boots. (Plus, I’m already 5’10”, so I don’t need any extra height!) You pretty much can’t go wrong with Dr. Martens because they’re so practical yet cool, last a long time, and are reasonably priced.”

Next: 16 New Boot Outfits I’m Adding to My Fall Outfit Checklist