I found similar styles from Levi’s, Madewell, and Good American.

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Fashion has always been cyclical—but this time, it only took 10 years to make that sartorial loop. It’s been a very 2016 2026. We’ve seen the resurgence of gladiator sandals, Ugg boots, and even graphic tees, so I’m guessing it’s not long before Miley Cyrus’s “dated” jean-and-shoe combo goes mainstream. Over the weekend, Cyrus donned a casual-cool outfit I suspect we’ll see a lot more of this fall. She wore a vintage sweatshirt, slim-fitting jeans in a chic indigo wash, and a pair of black Mary Jane flats; it was comfortable, cute, and, yes, something I would have worn 10 years ago.

Flats were one of the first 2010s trends we revisited, and, truthfully, they might be more popular now than they were then. This summer alone has seen multiple iterations blow up. Mesh, Tabis, sneaker-inspired, and glove flats have all spent time as this season’s It shoe, so it wasn’t Cyrus’s high-vamp Mary Janes that caught me off guard; it was how she styled them.

Cyrus’s jeans, which have spent the past decade being considered a fashion faux pas, truly surprised me. That narrow silhouette and skin-tight fit all but disappeared in the 2020s, being replaced by big, baggy jeans that brought an effortlessly cool vibe to anything they were worn with. And while I will always love a wide-leg (and plan to keep wearing them), I can’t deny the truth: Slim-fitting jeans are making a slow but steady return. Cool-girls like Hailey Bieber and Charli XCX have reintroduced them to their wardrobe, as have forever-fashion icons like Jennifer Aniston—it’s only a matter of time before everyone else catches on.

To get ahead of the trend, you can shop more cigarette and slim-straight jeans inspired by Cyrus’s pair below. Plus, some modern flats that bring the throwback style into 2026.