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

Josephine Hadjiloucas's avatar
By
Published In Buying Guides
@borislavasekova wearing Mary Jane flats, stovepipe jeans, and black top
(Image credit: @borislavasekova)
Jump to category:

I've noticed an uptick in jeans-and-ballet-flat outfits, whether it's IRL riding the subway or just scrolling IG. Maybe it has something to do with fall inching closer and closer, or we've grown tired of the same old summer 'fits and are once again 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.

Taking notes from the style sets in London and Stockholm, three denim styles stand out the most. Hint: They don't include skinny jeans (though they are on the comeback) or bootcut (sorry, my fellow Gen Zers; I know you love a little flare). What I will say is that each one has the makings of a closet staple: versatile, timeless, and reliable. I call on editor-loved brands like Agolde, Levi's, Kahite, and so much more.

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

Latest Videos FromWho What Wear

The Best Jeans to Wear With Ballet Flats in 2026

'90s Stovepipe

@borislavasekova wearing Mary Jane flats, stovepipe jeans, and 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. While yes, this slim-to-straight silhouette is reminiscent of Jennifer Aniston's wardrobe in Friends, this style has become a 2026 staple.

Cuffed Dark-Rinse

@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

@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. A white T-shirt and a touch of leopard, and you're good to go.

Shop More Editor-Approved Jeans

Shop More Chic Ballet Flats

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!”