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.
-
I'm Not Going to Mess Around—These Are the 3 Nordstrom Anniversary Sale Items I Can't Stop Thinking About (They Will Sell Out)
Some of my favorites are already gone.
-
I'm a Shopping Editor—These 5 Nordstrom Anniversary Sale Finds Are Living Rent-Free in My Head
Kitten heels, burgundy flats, and more.
-
Keep This Between You and Me: I Just Found a $165 Alt for The Row's Viral and Sold-Out $1300 Heels
You're welcome.
-
If You Want to Look Like a Chic Fashion Person, Wear This Shoe Trend With Cropped Pants
Selena Gomez is on board.
-
24 Chic Under-$100 Nordstrom Anniversary Sale Finds That Are Taking Over My Fashion-Editor Text Group
Longchamp, Levi's, Madewell, and more.
-
Yeah, You *Have* Been Wearing Athletic Shorts With the Wrong Shoes This Whole Time
Here's the *right* way.
-
I Swear By Elegant Outfits—35 Standout Items That Would Fit Right Into My Closet
Here's to a chicer outfit rotation.
-
Forget Wimbledon Whites—at Centre Court, *This* Was the Summer Shoe Color to Wear With Dresses
It's not black either.
-
Flat Mary Janes Are Cute, But If You Want to Look More Sophisticated, Wear These Instead
As seen on Anne Hathaway in Manhattan.
-
Just so You Know, *This* Is the Denim Trend New Yorkers Wear With Loafers (Sorry, Skinny Jeans)
And they're on sale right now on Amazon.