Kate Greer & Peter Fenton
Perhaps one of the most interesting ladies on our list, artist and popcorn princess Kate Greer is a certified Cool Girl. She first stepped onto the TWAG scene as Jack Dorsey's longtime on-again, off-again gal pal, but has since found love with Silicon Valley billionaire and venture capitalist, Peter Fenton (who is sometimes referred to as Dorsey's "rival"). The creative babe is part of a New York art collective alongside Cleo Wade, Liza Voloshin, Margot, and Mia Moretti, and she also founded a popcorn company, Cheerie Lane Popcorn, on her family's corn farm in Iowa.