Shopping·3 min read

We Went On a Hunt For the Most Comfortable Holiday Party Shoes — Here Are Our Three Favorites

Naturalizer Holiday Party Shoes
Naturalizer
November 19, 2025

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Over the summer, one editor called these Naturalizer heels a wedding season must after dancing in them for 25+ hours at five different weddings. With holiday parties on the horizon, we had the team try out three of the brand’s fall/winter styles and report back. Here are the three shoes we’re telling everyone and their mother about.

Naturalizer Deesha Knee High Boots
Naturalizer

Deesha Knee High Boots...

“I can confidently say these are some of the most comfortable heeled boots I’ve ever worn. The fit was spot-on. The shaft hugged my calves without sliding down (an annoyance I’ve experienced with other tall boots), and the heel height struck the perfect balance between ‘elevated’ and ‘I can still walk like a normal human.’ What surprised me most was how they felt out in the wild. I spent an entire day exploring the city and my feet never once begged for mercy. There was zero break-in period. No stiff leather. No mystery blisters. They genuinely felt like boots I’d owned for years, already molded to my foot and ready for whatever the day threw at them. Style-wise, they’ve quickly become my go-to this season. I’ve been pairing them with midi dresses, long coats, and even wide-leg trousers, and every outfit instantly looks more pulled together." — Sarai Thompson ($290)

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Naturalizer

Ines Pumps

“Loafers you don’t need to break in? Actually groundbreaking. The first time I wore these heeled loafers, I spent eight hours in them and woke up the next morning to zero blisters and zero arch pain. Since then, I’ve danced in them, walked multiple city blocks, and spent a full day at a museum with the same result. The style is also perfect for elevating a casual jeans look or for heading to the office. I especially like the modern buckle element. The heel height is also ideal for multiple occasions, giving me a nice lift without feeling overdone. One thing to note: the brown patent leather is prone to creasing, but it hasn’t bothered me in the slightest.” — Abby Drozd ($125, Naturalizer)

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Naturalizer

Pixie Mary Jane...

“This is my favorite hybrid shoe: part Mary Jane, part heel, and an all-around great choice for when you want a little lift without the pain. The pointed toe is chic, the higher vamp has complete coverage, and the strap is adjustable and comfortable. I was also really impressed with my lack of blisters after a night out in these. So far I’ve been pairing them with long skirts and tight leather leggings, but I’m excited to wear them with jeans and a sweater for a dressy-casual look.” — Alessandra Rey ($115, Naturalizer)

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