Madeline, 28

“I’m wearing an Earl Grey coat, Nikki Chasin dress, Prabal Gurung turtleneck, Staud handbag, Miista boots, and ASOS hat. The best outfits are born from experimentation. You can churn out the most interesting looks by playing around with unexpected silhouette pairings, old and new pieces, and funky small accessories. I am super inspired by history and costume design throughout the ages, specifically in American film. My winter wardrobe is based on everything from A Love Story to Clueless to Little Women.”