At the Whitmore Historical Costume Ball, the characters are dressed as follows: Elena Gilbert is Anne Boleyn, Damon Salvatore is Henry VIII, Stefan Salvatore is James Dean, Caroline Forbes is Bonnie Parker, Tyler Lockwood is Clyde Barrow, Tessa is Cleopatra, and Dr. Wes Maxfield is Dr. Jekyll.
At the Whitmore Historical Costume Ball, the necklace Elena is wearing is the same necklace America Ferrara wore throughout the television series Ugly Betty. The necklace is made of pearls with a large gold letter "B" and three teardrop pearls dangling from the bottom of the "B".