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.

What to wear with loafers


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Wear high-heel loafers with a minidress for a cool-girl retro look.

Did Gucci start this trend? It's very possible.

These are practically a neutral in my book.

Cool high-heel loafers


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Loafers are a fresh take on the white heel trend.

I can't think of many outfits these wouldn't go with.

Emma Roberts shoes



Emma Roberts found the perfect shoes to wear with a denim skirt this fall and winter.

The more snakeskin right now the better.

More snakeskin, in case you're as obsessed as I am.

Winter shoes to wear with jeans


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Could this be the new It heel style to wear with jeans?

On trend, affordable, and waterproof.

Another '90s-inspired style that I support.

High-heel loafer outfit


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Metallic loafers are a fun take on the trend.

I wouldn't be against wearing this out in the show with soles like that.

Of course Gucci made the most "extra" pair on the list.

Lucky you—this pretty pair is on sale.

If you want something more classic than trendy, these are for you.

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