Fashion Sofia Richie Shows Us How to Wear Sweats and Heels Welcome to "Who Won Fashion Today," where we award the boldest, best dressed person of the day. Winning fashion doesn't necessarily mean you're wearing the most expensive, trendiest, or prettiest dress. Rather, we reward risk-takers—those that stay true to their personal style and make us go, "Now THAT is a LEWK.” By Ruthie Friedlander Updated on January 20, 2017 Pin Share Tweet Email Photo: David M. Benett/Getty Dear Sofia Richie, I don’t know you or your style very well yet, but I want to congratulate you on your first win in our daily column, “Who Won Fashion Today.” Sofia Richie, Sistine Stallone, and Cameron Dallas Walk Dolce & Gabbana’s Show GOR/GC Images Wearing sweatpants with heels is something I very much admire, and your '90s throwback mini Louis Vuitton backpack was oh-so-wonderful. I look forward to seeing you featured frequently for your youthful, fashionable flare. Xoxo, InStyle.com Was this page helpful? Thanks for your feedback! Tell us why! Other Submit