Some shoes earn a permanent spot in the rotation, and for me, classic loafers have been that pair for years. They work with everything I own and quickly became an in-office staple. I’ve worn mine through more busy fashion months with busy walking days than I can count. Lately, though, I’ve noticed the best-dressed people I know swapping their flat pairs for a version with a little lift.
Enter the heeled loafer. It keeps everything we love about the original (the penny strap, the polished leather, the menswear ease) and adds a block or kitten heel that makes even the simplest outfit feel more finished. Don’t worry, your flats aren’t getting retired. This is just the pair I’d buy next. Ahead, see my favorite styles at every price point.
Our Favorite Styles:
Miu Miu
Croc Embossed Leather Loafer Pump
Miu Miu is the reason I started paying attention to this trend in the first place.
Saint Laurent
Costume Pump
A splurge in burgundy, the color I can’t stop wearing this fall.
Tory Burch
Vintage Heeled Loafer
Tory Burch’s vintage heeled loafer is the pair I keep seeing on fashion people.
A kitten heel that feels like they were designed for walking the city.
Proenza Schouler
Esme Loafer Pump
Proenza Schouler always gets the minimalist version of a trend exactly right.
ZARA
Leather Heeled Loafers
Real leather heeled loafers are always worth snapping up fast, especially when they’re under $150.
Tory Burch
Double T Logo Loafer Pump
This style is instantly recognizable in the best way.
cos
Angular Leather Heeled Loafers
The brown eel effect makes these look way more expensive than they are.
Stuart Weitzman
Vera Loafer
Stuart Weitzman makes heels you can actually walk around the city in.
Anonymous Copenhagen
Grenadine Shiny Lamb
The shiny espresso leather on these is so rich.
Tory Burch
Leather Vintage Heeled Loafer Pump
I love how these look like a pair you’d find at the best vintage shop in Paris.
STEVE MADDEN
Wallace Black Eel
Another eel finish and massive heighnt.
Jeffrey Campbell
Smithson Loafer Pump
The distressed vibe make a classic feel a little cooler.
Tony Bianco
Fenix Chocolate Venice
Chocolate brown is the shade I keep reaching for this season.
Manolo Blahnik
Cleofelo Loafer Pump
Manolo Blahnik always does it right.
GH Bass
Tessa High Heeled Penny Loafer
The penny loafer brand finally gave us a heeled version, and I’m so here for it.
Madison Maison
Leather Hidden Bit Heel Loafer
The subtle bit detail makes these feel so polished.
Kate Spade
Penni Heeled Loafer
A classic penny loafer with just enough lift.
Camper
Escandalo Loafer Pump
I’d wear these with straight-leg jeans and a cropped trench all fall.
Bared Footwear
Alethe Dark Oak Croc Emboss Leather Low Heels
Croc-embossed leather in dark oak is my idea of the perfect fall shoe.
Saint Laurent
Le Loafer Pump
A polished pump with all the ease of a loafer.
Bernardo
Nevaeh Loafer Pumps
An easy loafer pump you’ll wear with everything from jeans to tailored trousers.
ASOS DESIGN
Speed Mid Heeled Loafers
A black croc loafer at this price is an easy way to try the trend.
Bernardo
Safi Loafer Pump
The kind of pair you can wear to the office and straight to dinner.
Vince Camuto
Geanna Loafer Pump
A heeled loafer this easy is the one I’d wear on repeat all season.
Zara is always my first stop when I want to test-drive a trend.
A loafer pump that looks so much more expensive than it is.
Prada
Platform Loafer Pump
A little platform gives you height without sacrificing comfort.
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