Taylor Swift Brought Back the Shoe Trend Millennials Were Obsessed With in 2014

It's rare, but some things truly never go out of style. They may languish in closets or at resale shops, but sooner or later, they reemerge, taking their rightful spot back into the rotation. One such piece is, of course, the heeled loafer. While its flat-soled cousin has been a fashion girl mainstay more recently, Taylor Swift, millennial cat queen, and style chameleon is officially bringing back her go-to shoes from 2014. 

Back when I was walking through the west village with 1989 (released in October of 2014) blasting in my ears, you can bet I was wearing heeled loafers—and let's face it, probably a red lip and ray bans—channeling Ms. Swift in all of her new romantics' glory. Feel free to agree or disagree with me that 1989 is her best overall album (okay, fine, the Longpond Studio sessions are a revelation), 2014-era Taylor's fashion is undoubtedly iconic, living rent-free in my mind, along with the lyrics to the entire album. 

Fortunately, you don't have to wait until midnight to start shopping (or digging through your closet) for this key millennial fashion staple. We've rounded up our favorites below—they'll pair perfectly with that classic red lip you like.

Then:

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(Image credit: Getty Images)

Swift had an obsession with high-heeled loafers and oxfords in 2014. 

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(Image credit: Getty Images)

Another 2014 example of her adoration of the shoe trend. 

Now:

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(Image credit: Getty Images)

A modern version of the trend, these chunky Prada loafers are thoroughly 2022. 

Shop Heeled Loafers

Up Next: It's Unanimous: These Are Officially the Best Red Lipsticks That Money Can Buy

Freelance Writer

Drew Elovitz is originally from Pittsburgh, Pennsylvania, but has spent the last decade living and working in New York City. She earned a master's degree in media and popular culture from New York University, then began her career on the internet as the Twitter voice of Barbie. She worked previously at Who What Wear as the director of content strategy and also spent several years leading the social media teams at Teen Vogue and Entertainment Weekly. You'll find her byline on the site around topics such as celebrity fashion, must-have basics, beauty favorites (particularly nail polish), and wellness tips and tricks. Her personal style tends to favor the classics: She loves crisp white button-downs, sneakers, and skinny jeans—and no look is complete without a great pair of oversize sunglasses and a trusty leather jacket. After she finishes reading the entire internet every day, she can be found dining out at her favorite restaurants, trying new beauty treatments, or indulging her historical-fiction habit.