Our favorite photo of the week belongs to Star Trek: The Next Generation actor Wil Wheaton who shared an uber nerdy image of himself wearing ankle watches (with friendship bracelets!), acid-washed jeans, and a ratty Depeche Mode tee. We’ve featured the image of the Stand by Me star after the jump, along with photos of other pop culture idols and their (mostly) regrettable teen fashions. It’s a snapshot of simpler times, before the stylists and PR managers thoroughly preened them. See what a few of your favorite, famous teen heroes were wearing back in the day, below.
Wil Wheaton
“Me in 1987. For those of you keeping score at home, that’s two friendship bracelets on my ankle, keeping the WATCH I PUT THERE ON PURPOSE company, SIX total watches, and a Depeche Mode t-shirt tucked into my acid-washed jeans.”
Alyssa Milano
The 16-year-old Who’s the Boss? star wore acid-washed denim (rolled-up, of course) and a Teen Steam-era crop top.
Justin Timberlake
No suit and tie for 16-year-old J.T. — just a frosted-tipped fro, sports jersey, bling, and a smile. Stylist: mom?
Natalie Portman
Teenage Padmé wants all your sweaters.
Michelle Williams
Neon, spandex top, with mock-turtleneck — and a sassy face that Toddlers & Tiaras would be proud of.
Angelina Jolie
Eighth-grader Angelina looks like she’s prepping for Trader Joe’s university in a Hawaiian shirt. Her poofy, polka dot hairband looks adorable.
Joseph Gordon-Levitt
JGL was all about the blazers and newsboy hats.
Winona Ryder
A hairsprayed-to-hell home perm and ugly, silk button-down.
Neil Patrick Harris
Doogie Howser let his nerd flag fly in a Dick Tracy tee and round, wire-rimmed glasses.
Jay-Z
Young Hov was a hype man for mentor Jaz-O when this photo was taken in 1988, which is how he could afford all that gold. Don’t be jelly of that Giants hat, Brooklyn Nets.
Kurt Cobain
Clearly young Cobain wore his weird on the inside. His bowl haircut is kind of cute, but his guitar was still his greatest accessory.
Sarah Michelle Gellar Prinze
Overalls worn the 1990’s way, with one strap down.
Amy Poehler
We can forgive the wall of bangs and boring sweaters, because it’s Amy.
Tina Fey
Fro, all-floral dresses, and choke-me turtlenecks.
David Bowie
Shaggy hair, tons of tweed, and skinny tie-wearing teen Bowie looked prettier than you ever will.