Billie Eilish Gives Schoolgirl Prep a Subversive Edge

Billie Eilish brought a new take on preppy dressing to the red carpet last night right alongside a new relationship milestone. At the Lose Angeles premiere of her new concert film, Billie Eilish—Hit Me Hard and Soft: The Tour (Live in 3D) made her red carpet debut with boyfriend Nat Wolff in an artfully layered ensemble that mixed “prep” with “punk” and a little bit of “jock” sprinkled in for good measure.

Eilish’s layered ensemble featured a white collared dress shirt layered beneath an oversized, emerald green Prada polo. The star paired the pieces with a pleated black knee-length skirt, continuing her recent academia-inspired aesthetic. A silver wallet chain and layered rings added a rebellious touch of punk to her look.

For another fashion-related twist, Eilish completed her outfit with a pair of vibrant red tube socks. Trimmed in navy blue. Her cream kitten-heeled pumps, featuring ombré gray toes and sneaker-like front laces added a subversive athletic touch.

As of late, Eilish has been on an academia-influenced style streak. The singer’s recent looks have encompassed iterations of classically preppy pieces, from button-down shirts and ties to pleated trousers, blazers, and tall socks. Despite her new aesthetic, Eilish has remained loyal her penchants for dark colors, oversized silhouettes, and grunge influences—making this latest fashion chapter an additional layer of her edgy sense of style.

As for the romance? Eilish and Wolff, a musician and actor, have been friends for years. He even appeared in her 2024 “Chihiro” music video, and his musical project with brother Alex Wolff opened for Eilish on select dates of her Hit Me Hard and Soft tour. Its unclear exactly when the relationship turned romantic, but fans began suspecting the two were a bit more than friends in 2025 after a steady stream picture of the pair canoodling throughout the world hit the internet. Last night marks the pairs red carpet debut.