Lizzie McGuire (2001)

S1E13 Come Fly With Me

Gordo, ever the individualist, develops a fascination for the lounge culture of 1950s and '60s Las Vegas, inspired by icons like Frank Sinatra and the Rat Pack. Although Lizzie and Miranda are initially unimpressed, they gift Gordo a Rat Pack CD. To their surprise, Ethan Craft enjoys it during a bus ride, prompting the girls to rethink their stance. They soon adopt the era's fashion, and while Gordo appreciates their newfound interest, he worries it might become just another trend. Unfortunately, his fears are confirmed as Ethan influences the boys to sport Sinatra-style hats and embrace the music, even leading Kate to seek fashion advice from Lizzie and Miranda.