Never Been Kissed

Jossie Grossie flashes back to her ’80s school dance in an explosion of puffy pink taffeta. The added lace makes it look… classic?

Mean Girls

Kudos to Janice for rocking the purple suit and bowtie, but we wouldn’t necessarily choose her crazy get-up (or Damian’s matching ensemble) for a Homecoming Queen. At least she had the last laugh!

Napoleon Dynamite

Tina switched her signature side ponytail for a crimped-out up 'do. The pink lace and princess sleeves are a bit outdated. This awkward scene makes us laugh every time, but we do appreciate how she matched her earrings to the dress.

Ten Things I Hate About You

Bianca was totally on-trend for the ’90s crop top ensemble, but the tulle mix? We love her dad’s confused reaction.

Glee (Season 4)

Kitty Wilde was ready for her debut in this over-the-top emerald high-low dress. As if the gown wasn’t daring enough, she styled it with a diamond-accentuated fur coat. Interesting.

Romy and Michele’s High School Reunion

These funny girls aren’t necessarily looking forward to the reunion, but we’re always looking forward to what they’ll wear. Is that a boa around the hem of the pink dress? These metallic numbers make us chuckle every time.