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:
Swift had an obsession with high-heeled loafers and oxfords in 2014.
Another 2014 example of her adoration of the shoe trend.
Now:
A modern version of the trend, these chunky Prada loafers are thoroughly 2022.
Shop Heeled Loafers
Cannot possibly add these to my cart fast enough.
Truly a classic option.
A stylish way to get a leg up.
Another perfect platform.
These look way more expensive than $50.
A monochrome spin on the horse bit style.
Trendy yet timeless.
The most elegant shoes ever made.
Practical yet stylish.
It's hard not to love white loafers with contrasting black heels and gold embellishments.
Sleek and simple.
A little sparkily, a little pilgrim, a lot chic.
Up Next: It's Unanimous: These Are Officially the Best Red Lipsticks That Money Can Buy
-
Back to School: 5 Collegiate Shoe Trends That'll Be Everywhere This FallChic, comfy, and compliment-guaranteed.
-
I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds FromReplica Store, Zara, and H&MDid I mention they're under $250?
-
7 Things I Want From Reformation After Seeing These French It-Girl OutfitsIf I can't be in Paris this fall, I can at least dress like I am.
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall ClosetStylish sweaters and suedes ahead.
-
These 32 Chic Zara Fall 2025 Shoe Finds Are the Key to Looking Like a Fashion Person—Good Luck Picking Just One PairPrepare for endless compliments.
-
These Are the Only Labor Day Weekend Sales That Matter—Shop the Best Deals Thanks toReplica Store, Madewell, J.Crew, and MoreSave big on fall staples.
-
Predicting Taylor Swift's Wedding Dress: 5 Styles That Feel So HerIt's a love story, baby, just say yes—to the dress.
-
Taylor Swift Got Engaged Wearing This $17,000 Watch With Dozens of Diamonds—Take a Close-Up LookIt'll never go out of style.
