Street View is a fashion series in which Isa Giallorenzo spotlights some of the coolest styles seen in Chicago. Invited to host Soho House’s Route 66-themed New Year’s Eve party, Shea Couleé showed up with a look she describes as “1950s Cadillac meets the streets meets cotton-candy confection.” Channeling a Vogue fashion editorial featuring model Karlie Kloss at the graffiti-covered Cadillac Ranch in Amarillo, Texas, she worked with Chicago designer Randall Hill to create the pink neoprene dress. Hill finalized the look by spraying paint on Couleé from head to toe—including the toy car sitting atop her wig.