As we attempt to prepare ourselves and our wardrobes for the impending Fashion Week (and autumn to follow), it feels like planning outfits for the first day of school. Long before the days of Insta-selfies and street style, clothes selected for the much-anticipated return to the hallways carried serious weight, sending coded messages about our vacations (see: concert tees, friendship bracelets, tan lines) and setting the tone for the school year ahead. Questlove captured it best for us earlier this summer, at Madonna’s party at Harlow: “You know, the night before the first day of school, that outfit in your closet you can’t wait to rock?” he remembered. “Seventh grade. ‘Everybody’ was on. And my outfit kept staring at me. I was staring at my outfit all night, just imagining I was gonna rock people in the morning when they saw my outfit.” Read on to find out what Questlove wore to rock his classmates, along with Courtney Love, Jenna Lyons, Zac Posen, and several other designer’s favorite back-to-school looks. Then tell us about yours in the comments.