“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.”
The 16-year-old Who’s the Boss? star wore acid-washed denim (rolled-up, of course) and a Teen Steam-era crop top.
No suit and tie for 16-year-old J.T. — just a frosted-tipped fro, sports jersey, bling, and a smile. Stylist: mom?
Teenage Padmé wants all your sweaters.
Neon, spandex top, with mock-turtleneck — and a sassy face that Toddlers & Tiaras would be proud of.
Eighth-grader Angelina looks like she’s prepping for Trader Joe’s university in a Hawaiian shirt. Her poofy, polka dot hairband looks adorable.
JGL was all about the blazers and newsboy hats.
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.
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.
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.
We can forgive the wall of bangs and boring sweaters, because it’s Amy.
Fro, all-floral dresses, and choke-me turtlenecks.
Shaggy hair, tons of tweed, and skinny tie-wearing teen Bowie looked prettier than you ever will.