40 Incredibly Awkward Celebrity Prom Photos (Why Did Jaden Smith Wear Leggings?)

Just like you, your favorite celebrities went to prom back in the day. Some are cute and some are beyond cringeworthy.

Will Ferrell Is Obviously Prom Queen
Comedy started really early with Will.

Is It Possible That Matthew McConaughey Was Once Dweeby?
As McConaughey said in “Dazed & Confused,” “That’s what I love about these high school girls, man. I get older, they stay the same age.

Trey Songz Keeps It Classy With A Black Suit
Trey Songz admitted in an interview with MTV that he did his girlfriend’s eyebrows and cut his friends hair before prom. Talk about accommodating his loved ones.