Miley Cyrus Wore This Divisive 2000s Shoe Trend on the Grammys Red Carpet

Miley Cyrus isn’t just an early 2000s music icon—she’s an early 2000s fashion icon, too. Case in point? The "Flowers" singer strutted the 2025 Grammys red carpet in a pair of peak Y2K footwear: metallic wedges. Cyrus, dressed by her longtime stylist Bradley Kenneth, wore a leather halter gown, courtesy of Saint Laurent by Anthony Vaccarello, paired with the controversial wedges. Cyrus' choice of footwear, Saint Laurent’s Salomé wedges, completed the full head-to-toe maison look, with additional sparkle coming from jewels by Tiffany Co.
Shop Miley's Wedges
Cyrus has come a long way from her Hannah Montana days (even though her starlet-inspired chunky highlights may beg to differ!). The artist, who won her singular award tonight (Best Country Duo/Group Performance for "II Most Wanted" alongside Beyoncé), clearly paid homage to her breakout role on the Disney Channel series. Don’t forget where you came from, folks!
You can keep up with the rest of our Grammys red carpet coverage on our 2025 live blog.

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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