As soon as the sixth grade started, I was acutely aware of the tension between girls and boys, and the competitiveness between girls.

“At 12, I switched from Waldorf to public school. Mariah Nielson, curator and design historian: I loved it and saved it for picture day, when all the kids informed me that wearing red and black on Friday meant you were a whore. It was red and black with little flecks of gold. In sixth grade, my mother made me a Hawaiian shirt out of fabric I had picked out. I was a freckled, auburn-haired kid, and I definitely didn’t feel confident in my appearance. When I was coming-of-age, California blondes were it. The John Hughes films I made were much closer my middle-school experience. Since I was working so much, I didn’t really pay much attention to the issue of popularity at school. “By the time I was in high school, I was deemed the most popular teenager in America. (Turns out, Judy Blume struggled in middle school, too.) Here, 16 women on the shoes, bags, clothes, and brands they loved above all else. We talked to a slew of mean girls, nerds, and outcasts, plus the self-described “second or third most popular girl in my high school.” Now they’re artists, writers, actors, and athletes.

Years later, they can still carry the weight of fitting in or the fear of standing out they capture bygone struggles with body image and gender presentation, and symbolize a growing awareness of race and class. Even after you’ve traded in school uniforms for business-casual ones, given up on getting that trend right, and finally put down that hideous but really, really expensive bag, totems of popularity don’t quite lose their power.

Being flat chested is a status symbol