Chrissy Teigen & Kate Upton – Pageant Princess and Marilyn Monroe

Heidi Klum’s Halloween parties are the stuff of legends, with celebrities often pulling out all the stops. When Chrissy Teigen and Kate Upton made unforgettable appearances in 2011, they understood the assignment. Chrissy, known for her hilarious wit and strong social media presence, took us on a quirky trip down memory lane, dressing as a pageant princess straight out of the controversial reality show “Toddlers & Tiaras.”

The oversized crown, the sparkly sash, and Chrissy’s playful portrayal reminded everyone of the absurdities of child beauty pageants. Meanwhile, Kate Upton, Sports Illustrated model and actress, channeled the timeless beauty of Marilyn Monroe with her signature blonde curls and iconic white dress.