Slim Bootcut Jeans Are So Back—This Is the Flat-Shoe Trend They Look Best With
Not ankle boots, not loafers—this is the shoe trend that makes slim bootcut jeans look the most 2026.
This summer, I made a conscious effort to give my jeans a break and live in shorts, skirts, and dresses instead. Why? Honestly, I needed a reset. By the time winter rolls around, I'm usually so burned out on my denim collection, and I want to make sure that doesn't happen again this year. But with fall already on the horizon, I'm starting to think about bringing jeans back into my rotation and figuring out which styles I want to wear again. One silhouette that's quickly made its way to the top of my list? Slim bootcut jeans. I spotted Kate Moss wearing a pair this week in London, and I happen to have a favorite pair from Levi's.
Finding the shoe that makes slim bootcut jeans look chic rather than "dated" can feel a little tricky, especially when it's too early to pull out boots. However, Moss makes it seem easy by opting for classic black ballet flats. The very traditional, timeless style perfectly grounds the late '90s to early 2000s silhouette, making them feel modern again. Plus, since I live in New York City, where walking is my preferred mode of transportation, there's really no more comfortable choice than ballet flats—well, other than sneakers, which you won't find me wearing with denim.
When it comes to styling the flats-and-jeans look, I could take inspiration from Moss again and finish the outfit with a tie-neck button-down shirt and a leather top-handle bag. Or, I could go for a Chloé-esque blouse with a slouchy shoulder bag, a white T-shirt with a trench coat, or a fitted sweater with a suede belt. The styling possibilities are endless.
Scroll on to discover and shop the chicest slim bootcut jeans and ballet flats to invest in now.
Shop Bootcut Jeans and Ballet Flats:
Recreate Moss's look with this classic style.
You probably know by now that Who What Wear editors love these because they're an affordable alternative to Kendall Jenner's favorite The Row Stella Flats.
Giving boho chic.
New and already a best seller.
There's nothing else to say beside that these are perfect.
No one will believe you when you tell them that these are from Sam Edelman.
I love this vintage-looking wash.
Ever since I saw woven flats from The Row I've been obsessed with them.
These look so flattering on any body type.
You can't go wrong.
