This "Ugly" Heel Trend Is Quickly Emerging
In my humble opinion, there's no better flat shoe style than loafers. Especially during the fall and winter months, I'd say that it's the shoe style I reach for the most. Because of this, I'm naturally often inclined to put loafers in my stories, and I've recently noticed that a new loafer trend is emerging right now: loafers with heels. Now, some may consider this '90s throwback to be an "ugly" shoe style, but I've come across so many loafers with heels from the coolest of brands lately that I can say with confidence that we have a trend on our hands.
Not only am I spying high-heel loafers on the market a ton lately, the street style scene is crawling with them, and even Emma Roberts just endorsed the trend. So, if you're reluctant to give the high-heel loafer trend a try this winter, take my word for it: They're a thing. (They're also a very comfortable, walkable thing, so how's that for bonus points?)
Keep scrolling to see how people are styling the trend and to shop the very best pairs along the way, chosen by yours truly.
Wear high-heel loafers with a minidress for a cool-girl retro look.
Loafers are a fresh take on the white heel trend.
Emma Roberts found the perfect shoes to wear with a denim skirt this fall and winter.
Could this be the new It heel style to wear with jeans?
Metallic loafers are a fun take on the trend.
Next up, the best fall shoes for your feet, according to a podiatrist.

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
Gigi Hadid Wore the Fall Shoe Trend That Looks Best With Full-Length JeansClassic.
-
I'm a Senior Shopping Editor—29 Pieces I'm Eyeing Ahead of Black Friday That Will Get You Envious Stares and ComplimentsThese are guaranteed to elevate your wardrobe.
-
All the Coolest Girls I Follow Are Wearing This "Dated" Shoe Trend With Jeans, Dresses, and SkirtsGive your pointed-toe heels a break, and wear this style instead.
-
Not a Bomber, Not a Trench: Everyone With Taste Is on the Hunt for This "Dated" Leather Jacket TrendI just ordered one from Revolve.
-
Here It Is: The New It-Girl Way to Wear Jeans and a Pair of HeelsSofia Richie gets it.
-
People Always Compliment My Winter Outfits for Being Polished—These 7 Chic Items Are My SecretSimple pieces, big impact.
-
I Walk Over 5 Miles a Day Working in Manhattan—Here's an Editor-Approved City Girl's Guide to Fall ShoesPlus, how I'd style them.
-
These Are the Surprising Shoe Trends Gen Z Is Styling With Everyday Outfits for the Rest of 2025Niche, weird, and unconventional.

