6. Chrissy Teigen & Kate Upton
This year’s Heidi Klum Halloween bash has been going on for so long that Kate Upton was seven years old when it all began. Fast forward to Halloween 2011, when a 19-year-old Upton posed with the lovely fellow model, 26-year-old Chrissy Teigen, for the 12th annual celebration.
Admission to a Halloween party at the PH-D Rooftop Lounge at Dream Downtown in New York City is contingent on wearing a well-thought-out costume. Teigan’s pageant princess attire from the television show Toddlers and Tiaras is a clear demonstration of her intellectual abilities. With her Marilyn Monroe outfit, Upton scores a few more style points, and the addition of the zombie element makes it a Halloween-appropriate costume as well.