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These Are the Heeled Boots You Won’t Hate If You Usually Live in Sneakers

Allie Flinn

December 11, 2018

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Photo: Getty Images/Aleksandr Zotov

My love affair with sneakers is well-documented. But I wasn't always like this. Just a couple of years ago, the idea of wearing sneakers anywhere aside from the gym made me feel nauseous. I would strap myself into the most painful shoes, and I took pride in the fact that I was sacrificing personal comfort for looking good.

Fast forward to today, and I'm now the kind of person who wears full-on workout clothes even if I'm not going to work out. (I dare someone to tell me leggings aren't real pants.) So anytime I'm required to wear footwear that's not a sneaker, I get a little annoyed/concerned about the well-being of my feet. I say "required" like I couldn't get away with wearing sneakers basically anywhere in Los Angeles where I live, but sometimes even I want to switch it up from sneaks and put on some cute heels.

That said, I'm not about to strap my feet into torturous shoes anymore. Since it's now winter time, I'm adding heeled boots to my footwear rotation. Here are the pairs I, a devoted sneaker lover, actually find comfortable enough to wear on the regular.

Everlane Women's Boss Boot, $235

When I saw the white patent leather iteration of these boots I immediately turned into a living heart-eye emoji. The two-inch heel gives me a little boost in the height department without making me want to inject my feet with Novocain. And despite the pointy toe, they don't smoosh my toes in an uncomfortable way.

Zara High Heeled Leather Ankle Boots with Elastic Side, $100

Normally, I'd never choose something higher than two-to-three inches for everyday wear. (Okay, let's be real, I'd never choose anything higher than the lift on my APLs.) But these chunky Zara boots are incredibly comfy thanks to the block heel and the elastic sides.

Nicole Miller Rozilyn Black Suede Over the Knee Boots, $600

When I want to bring it but also don't feel like strapping my feet into uncomfortable heels, I reach for these boots. Yes, the heel is really high, but I was surprised by how comfortable they are. (I mean, a six-inch heel is never ever going to be as comfy as a pair of Vans, but these come pretty close.) I've worn them out to a dinner date and then for a walk along the Venice boardwalk, and I didn't want to throw myself in the ocean—a good sign for both the romantic and footwear elements of the night.

Comfy shoes are one way to show your feet some TLC. Another is exfoliation (yep, seriously). Oh, and don't forget about cozy socks.