Quintessentially '90s, Timberland boots have endured through the decades from throwback outfits worn by Aaliyah and Missy Elliot to modern looks worn by Rihanna, Jennifer Lopez, and Hailey Bieber. Whether you're rocking a pair of baggy jeans or a cute dress, go for the classic 6" lug-soles, heeled versions, or a pair of overbuilt sneakers from the time-honoured brand.