The most iconic 1999 style moments turning 25 this year
CNN
From Pamela Anderson’s big pink hat to the all-leather dress codes of “The Matrix,” these are the standout looks that defined the end of the millennium.
In 1999 fears were rising about the end of the world — but if civilization had actually melted down thanks to an end-of-millennium technological apocalypse, at least we would have gone out in style. (Think tiny tube tops, platform shoes and ultra-wide-legged JNCOs.) It’s been 25 years since the ’90s closed out with an iconic year of film, television, music and fashion. Britney Spears redefined the pop star archetype, “The Matrix” enshrined a futuristic uniform of PVC trench coats and jet black sunglasses, and Lil’ Kim donned her infamous purple nipple pasty at the year’s MTV Video Music Awards. Here are 11 of the biggest style moments turning 25 this year. American teenage style has long loomed large in popular imagination, but 1999 was a canonical year for the high school genre thanks to a run of movies that included “10 Things I Hate About You,” “She’s All That,” “Drive Me Crazy” and “Never Been Kissed” as well as more subversive takes including “Cruel Intentions” and “But I’m a Cheerleader.” The costuming ranged from more realistic attire (“American Pie”) to a dose of camp (“Jawbreaker”), and there’s plenty of fashion moments to mine from each movie, from Larisa Oleynik’s two-piece red-and-pink prom look (pictured above) in “10 Things” to Sarah Michelle Gellar’s rich-girl vixen getups from “Cruel Intentions.” Some of the sartorial tropes became so played out that they were spoofed just two years later in “Not Another Teen Movie” — including, of course, the ugly duckling who removes her glasses and is suddenly a ten.