Hilary Duff’s ‘Outdated’ Styling Trick Instantly Elevates Baggy Jeans and Flip-Flops


Hilary Duff is a real millennial’s millennial.

Duff is about to embark on a world tour after the smash success of her intimate “Small Rooms, Big Nerves” mini-tour, where she performed early-aughts classics like “What Dreams Are Made Of” and “Come Clean” to sold-out crowds that still knew every word. She seems giddy to take this trip down memory lane with all of us, promoting her return to the stage by filming TikTok videos set to “Wake Up” and revisiting her iconic filmography with Vanity Fair. Talk about giving the people what they want.

The truth is that millennials never let go of our love of Duff’s old music or movies in the same way we won’t give up on the “millennial tuck” (aka the French tuck) that Gen-Z once declared outdated and cringeworthy. And Hilary Duff’s latest casual look is proof we’re right to hold on tight.

On January 30, the 38-year-old pop star was photographed running an errand in a classic white t-shirt and baggy blue jeans, unbothered by the way her relaxed denim pooled around her thin flip-flops. And yet, Duff looked far from sloppy in her casual uniform and lazy-girl claw-clip, thanks to the styling trick that takes less than five seconds.

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Hilary Duff in Los Angeles on January 30, 2026.

DUTCH/Bauer-Griffin

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