Prom season is almost upon us. Which means boys are renting tuxes and limos, girls are trying on frothy dresses, and everyone is prepping for an after-party filled with alcohol and lost virginities.

We kid. (Sort of.)

But the best thing about prom is having some of your worst fashion decisions preserved for all time on film ... and even celebrities aren't immune to that little personal nightmare.

From fried hair to awful gowns and even a tiara or two, the stars on this list would probably love a do-over. Let their pain be your schadenfreude -- and remember, embarrassing prom portraits are forever, but at least your mistakes aren't fodder for the whole internet.

Brad Pitt

Michael Buckner, Getty Images

Courteney Cox



Jason Merritt, Getty Images

Jennifer Aniston

Jemal Countess, Getty Images

Michelle Obama

Win McNamee, Getty Images

Natalie Portman

Kevork Djansezian, Getty Images


Cindy Ord, Getty Images

Taylor Lautner

Jason Merritt, Getty Images

Christina Aguilera

Jamie McCarthy, Getty Images

Will Ferrell

Skip Bolen, Getty Images