Here, alongside then-boyfriend Eric Erlandson, Barrymore was in her grunge ... sleaze. Drew Barrymore attended the 1998 Academy Awards in a black, low-back gown that gave pure '90s minimalism.

Announced December 10, Glossier's limited-edition Shadow Sticks were designed as an ode to the soft grunge look of the late '90s and early '00s. Think Courtney Love, Drew Barrymore, and—yes ...