The very first time I went clubbing in Manhattan, I wore sneakers. I was accompanied by three club rat girlfriends in LBDs and strappy heels, I had a confident strut, a vintage Jean Paul Gaultier mesh ...

Stars like Timothée Chalamet, who stepped out in Palm Springs earlier this month wearing head-to-toe Wrangler, with some cowboy boots to go with it—a departure from his typical red carpet vibe.