Not Skinny, Not Bootcut—the 3 Jeans Good Dressers Are Wearing With Ballet Flats From Now Until 2027

Josephine Hadjiloucas's avatar
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Last updated In Buying Guides
@borislavasekova wearing Mary Jane flats, stovepipe jeans, and a black top.
(Image credit: @borislavasekova)
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I've noticed an uptick in jeans-and-ballet-flats outfits, whether it's when I'm riding the subway or just scrolling IG. Maybe it has something to do with fall inching closer and closer, or maybe we've grown tired of the same old summer 'fits and are returning to a classic. Truthfully, there's nothing chicer than a pair of good jeans and comfortable flats. But just because it's a classic doesn't mean it has to be boring.

I took notes from the style sets in London and Stockholm, and three denim styles stood out the most. Hint: They don't include skinny jeans (though they are coming back) or bootcut. (Sorry, my fellow Gen Zers. I know you love a little flare.) Each one has the makings of a closet staple—versatile, timeless, and reliable—and can be found at editor-loved brands like Agolde, Levi's, and Khaite.

I've included the top ballet-flats trends of summer (shout-out jelly sandals and mesh flats) and chic color trends like baby blue and light pink. Oh, and of course, I found suede styles that will be perfect for autumn. Okay, without further ado, scroll on to shop the best jeans to wear with ballet flats.

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The Best Jeans to Wear With Ballet Flats in 2026

'90s Stovepipe Jeans

@borislavasekova wearing Mary Jane flats, stovepipe jeans, and a black top.

(Image credit: @borislavasekova)

The '90s trend isn't fading anytime soon, so if you've been skeptical, you might as well embrace it. The best place to start? A pair of '90s-inspired stovepipe jeans. Yes, this slim-straight silhouette is reminiscent of Jennifer Aniston's wardrobe in Friends, but the style has become a 2026 staple.

Cuffed Dark-Rinse Jeans

@fakerstrom wearing a double denim outfit from VRG GRL.

(Image credit: @fakerstrom)

I love dark-rinse jeans, so I didn't need convincing on that. But the cuff? That's another story. What truly sold me on this folded style was its sophisticated charm. Doesn't @fakerstrom look so elegant in this Vrg Grl double-denim look? Not to mention how cute the cuffed hem looks draped over a pair of flats.

Relaxed and Baggy Jeans

@nlmarilyn wearing baggy jeans, animal-print flats, a white tee shirt, and animal-print trench.

(Image credit: @nlmarilyn)

Maybe it's barrel, maybe it's mid-rise—the only thing that matters is if it's loose, relaxed, and oversize. This laissez-faire silhouette makes styling easy. With a white T-shirt and a touch of leopard, you're good to go.

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Josephine Hadjiloucas
Josephine Hadjiloucas
Assistant Shopping Editor

Josephine Hadjiloucas is a New York–based writer. She first interned at Who What Wear UK in 2024 and later joined Who What Wear U.S. as an assistant shopping editor after graduating from the Fashion Institute of Technology in 2025. When she isn’t covering the latest Gen Z trends or updating her under-$100 Nordstrom wish list, you can find her browsing the racks of NYC’s best vintage stores or rewatching Moonstruck for the 50th time. “Snap out of it!”