Olivia Rodrigo Gave The Slip Dress a Fall Twist With Boots

On August 6, the night of Olivia Rodrigo’s surprise show in New York City, she changed from one summer dress trend into another. First, in true Rodrigo style, she took center stage in a floral babydoll. After singing her greatest hits, the pop star tested summer-to-fall transitional dressing in a satin slip mini and knee-high boots. Opposites really do attract.

Outside Brooklyn’s famed pizza restaurant Lucali, paparazzi snapped Rodrigo looking every bit a punk-rock princess. While the pale pink silky slip shared the same thigh-sweeping hemline as her go-to dress silhouette, the upper half featured slim spaghetti straps and a plunge V-neck. Still, she styled the look like one of her babydolls—with grunge-inspired stompers.

Pairing the minimalist ’90s-inspired dress with pointy pumps—or perhaps her signature Mary Jane heels and socks set—would’ve been too obvious for the performer who has a penchant for style plot twists. So, instead, she chose tall black boots with a shiny leather finish, silver zippers up the sidewalls, and buckles atop the almond-shaped toes.