All the Cool Girls Had One: 16 Women on Teen Status Symbols

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. 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.

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. (Turns out, Judy Blume struggled in middle school, too.) Here, 16 women on the shoes, bags, clothes, and brands they loved above all else.

Molly Ringwald, actor and writer:

“By the time I was in high school, I was deemed the most popular teenager in America.

Since I was working so much, I didn’t really pay much attention to the issue of popularity at school. The John Hughes films I made were much closer my middle-school experience. When I was coming-of-age, California blondes were it. I was a freckled, auburn-haired kid, and I definitely didn’t feel confident in my appearance. In sixth grade, my mother made me a Hawaiian shirt out of fabric I had picked out. It was red and black with little flecks of gold. 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. I didn’t even know what that meant.”

Mariah Nielson, curator and design historian:

“At 12, I switched from Waldorf to public school. As soon as the sixth grade started, I was acutely aware of the tension between girls and boys, and the competitiveness between girls. I quickly understood that boys ‘liked’ girls with big boobs, that wearing tight or revealing clothes got you more attention, and that Keds had to be crisp white. I couldn’t achieve any of these things, as I was flat-chested, wore oversize hand-me-downs, and lived on a dirt road.”

Lisa Lucas, executive director of the National Book Foundation:

“I went to an almost entirely white private school when I was young. Everyone wanted to be Punky Brewster, and meanwhile, I loved her black friend Cherie. There was always something that people were doing with their hair that I couldn’t do. I was never gonna look like the girls on the cover of The Baby-Sitters Club, but in seventh grade I switched to public school, where I was suddenly surrounded by all these beautiful brown and black girls. I remember the ground shifting underneath me. What I had come up believing was hip changed in a minute, and I was in this real hurry to figure out how to do my hair and dress.

Grunge was big, Winona Ryder was huge, Heathers came out, but also, growing up just outside of New York City at a really peak moment in hip-hop was very influential to us. All the clothes were huge, everyone had to have Dunks. I was pretty nerdy, so I was actually grateful for the cues because I never had any fashion sense; it was a relief to know what to buy. In seventh grade, I got an oversize Charlotte Hornets Starter Jacket at the mall, and it felt perfect. Still, I spent a bit of time playing catch-up after switching schools, having this realization of, Oh, I’m great the way that I am, now I have to grow into it.”

Judy Blume, writer:

“For me, it was all about breasts. In the ’50, girls wanted to look shapely and older, more like mature women than girls. There was no way I could compete. I was small, skinny, and a late developer. ‘Did you hear, Judy swallowed an olive and six boys left town!’ boys would say. It took me a while to figure out that one, but it meant skinny me looked pregnant from swallowing an olive. I’m thankful now that breast implants weren’t around when I was young. I wonder if I would have asked for them. Recently, I went to my 60th high-school reunion, grateful for my small breasts (actually, one original breast and one implant thanks to a mastectomy, but still grateful).

My best friend from seventh grade is still my best friend. Writing In the Unlikely Event took me back to the ’50s and kept me there for five years. But even when I’m writing about contemporary friendships, the way kids feel about themselves is always important. I can tell you that I was thought to be popular, but inside I was a jumble of insecurities. I kept those feelings to myself, covering them up any way I could. Not exactly Sheila the Great, not exactly Margaret, but somewhere in between. Adolescence — thank god it’s over!”

Porochista Khakpour, novelist, journalist, and critic:

“When we moved to America from Iran, I evaluated and studied all that was cool, and I realized I would be outside of that. The girls were always tanning, but I was this other tan; I couldn’t have that particular blonde hair that everyone was obsessed with. Everything in L.A. was all about showing skin, and I was plagued by what to do with all my body hair. I didn’t really understand that people shaved or waxed, and I was so stressed about why I was like this that I never even asked my mother. Nothing terrified me more than a bikini for the longest time.

The popular girls wore jelly shoes, scrunchies in their hair, charm necklaces, Hypercolor T-shirts, and leggings. We didn’t have a lot of money, so I did what I could with scraps here and there: a cowboy hat, neon-orange soccer socks, lots of dollar-store bangles, plus thick glasses and braces and a mustache. I mostly hung out with my best friend, another outsider, watching a lot of old movies, making crank calls, and dreaming up our futures together.”

Elise Loehnen, head of content, Goop:

“I grew up in Missoula, Montana, and the closest Gap was in Spokane, Washington — clothes from the Gap were the pinnacle of coolness, because it meant that you either got to do your back-to-school shopping in another state or you were fortunate enough to travel. At 14, I went away to boarding school. There was a loose dress code, and it was easy to assimilate into that, particularly because J.Crew would bulk ship catalogues to the P.O. box. My parents, who don’t really buy into that stuff, were very gracious about letting me catalogue shop to fit in.”

Tina Dang, chef:

“I really, really, really hated cliques, and the cheerleaders made me want to throw up. At 12, I begged my mom to get me a pair of 10 Hole Doc Martens in blue. She thought they were pretty extreme and also hideous, but I thought they were the coolest thing, especially because the popular girls didn’t wear them.”

Jenna Weiss-Berman, podcast producer and co-founder of Pineapple Street Media:

“I was popular, but I was also an anomaly because I was a super-popular genderqueer gay kid. My queerness also contributed to my popularity, in that I wanted people to like me so that my gender presentation wouldn’t make them uncomfortable. So I would go out of my way to be friendly and accommodating, and I still find myself doing that. I think popularity, in many ways, is a form of self-protection. If you’re popular and you say something is cool, you can make it cool, and you can judge people who aren’t into the thing you’ve decided is cool. I was in sixth grade in 1994, and one day I came to school wearing my dad’s way too big corduroys and flannel shirt. The next day, almost everyone in the class came in wearing the same outfit. Kurt Cobain died a month later.

In the late ’90s, there were some very specific signifiers of butch coolness that I adopted: cargo shorts, Adidas shell toes, a wallet chain, ‘wife beaters.’ I also buzzed my head and bleached what was left, which was super cool until Eminem came along a year later.”

Doreen St. Félix, writer:

“I was probably the second or third coolest girl in my private, Upper East Side high school. It was all girls, and our teachers succeeded in creating this utopia where the smart, good girls are loved by everyone. An element of my coolness was that I was the scholarship girl and I grew up in Brooklyn, and that was just starting to become legible to a lot of the white girls who grew up on the Upper East Side. Longchamp bags were incredibly popular. I never had one, but I found ways to use the Brooklyn mystique to justify why I was still using a JanSport backpack at 17.

We wore uniforms, so accessories were super important, you had to find furtive ways to insert your style. Those $20 Hanky Panky thongs were really big. My parents are Haitian immigrants, and they were appalled by how much money my classmates were given for clothes and things. But lunch on the Upper East Side is really expensive, so sometimes I wouldn’t eat, or I’d get something cheap, and save that money to buy myself a Hanky Panky thong.”

Marilyn Minter, artist:

“I was one of the wild party kids, probably the instigator. I skipped school to go to the beach, was sent to the dean of students every week, and ended up in jail at 16. I secretly longed to be one of the popular, good kids, but didn’t have a clue how to go about it. I was never much of a consumer; the only thing I ever wanted was a sports car, which I got, used. It was a white Triumph Spitfire.”

Janet Mock, author, activist, TV host:

“Especially when you become a public figure, the strategic thing to do is to be self-deprecating and say, ‘No one ever liked me; I was the girl in the corner reading books.’ I was that, too, but I was also pretty well liked. In seventh grade, I remember coveting these platform Soda sneakers, but I wasn’t allowed to wear ‘girls’ clothes. Later, when I wore clothes that I felt best aligned with my gender expression, or had amazing silver eye shadow and plucked my eyebrows perfectly, I’d hear, Oh, you’re really pretty for a black girl, or, You look really good considering the fact that you’re trans.

“I came back in ninth grade and reintroduced myself as Janet; by spring, I was wearing women’s clothes frequently. I stood out, for sure, but there was some admiration for that, because in high school you really want to fit in. I regret it now, because my eyebrows have struggled so much, but pencil-thin eyebrows were what we all worked for. We’d tweeze before school started.

As the only black girl in high school, I could do things with my hair that the Asian and Polynesian girls couldn’t. I followed every single thing that Destiny’s Child did with their hair. I had the single, blonde highlights in the front; I had the Farrah Fawcett flip from ‘Independent Women’; I had the micro-braids from ‘Bug a Boo’; I had the cornrows from Say My Name.’ I had to get an after-school job in order to afford my hair-styling budget. Destiny’s Child were the height of popular culture, and a huge inspiration for us all. One of the coolest looks was an imitation of Beyoncé’s ‘Bug a Boo’ outfit; I wore mid-rise capri jeans with patches, an airbrushed T-shirt, and Candie’s heels.”

Mary H.K. Choi, writer and correspondent, Vice News Tonight:

“Growing up in Hong Kong, I worked so diligently to get to a certain social standing that by the time I turned 13, I was really popular, something of a known entity in the private-school scene. When we moved to Converse, Texas, I felt like I was being demoted. In Hong Kong, brands were huge, but also, as I grew up, bootlegs were so easy to come by that having a branded item lost a certain appeal. On my first day of school in Texas, I wore maroon, velvet bell-bottoms; a pale-yellow, vintage blouse; and platform shoes. Everyone else was wearing Girbaud jeans and K-Swiss sneakers. But, when I stopped caring so much about brands, boys, and jockeying for a weird social position, I started reading.”

Collier Meyerson, journalist:

“First, it was baby tees, then it was Paris Blues flared jeans, then the flared jeans became full-on bell-bottoms. When I got a pair of vintage, yellow, corduroy bell-bottoms, I wore them to school the very next day. No one said a single thing. Even worse, after school a bunch of us walked up to my friend’s really cool babysitter, and the first thing she said was, ‘Cool pants, Big Bird. Also, you know they’re on the wrong way? Zipper is supposed to go up the back.’ I was mortified.”

Akilah Hughes, comedian:

“Back-to-school shopping was something I always dreaded because I felt nervous to ask my mother for everything I wanted. By high school, I was aware that we didn’t have money. Sophomore year of high school, my friend gave me a Victoria’s Secret PINK hoodie. Paris Hilton had made tracksuit chic happen for my small Kentucky town. My hoodie was pink velour and had a bejeweled zipper. I thought it made every outfit look effortlessly cool and current.”

Aly Raisman, Olympic gymnast:

“I spent all of high school worrying about what others thought of me. I would go to school from practice covered in chalk and foam pit, and I felt self-conscious that I didn’t look as pretty or feminine as the other girls in my classes because I worked out a lot. A lot of girls started to wear high-waisted jeans with belly shirts or bra tops. I had the body for it, but never felt comfortable dressed like that. At the gym, GK Elite leotards were the coolest because they were the national-team brand. Now, I actually have a leotard line with them. Looking back, I hate how I wasted time feeling insecure.”

Laurie Simmons, artist:

“Conformity was essential (and very oppressive) in suburban Long Island when I grew up. Pappagallo shoes were the coolest. There was a real range of wealth in the community, from working class to upper-middle class, and the popular girls had the shoe in up to 20 different colors. They were $12 a pair, but I was one of three sisters, and my mother wouldn’t go higher than $5 for shoes. Somehow, I found out about a Pappagallo outlet store, and I got my mother to drive me. All of the shoes were damaged and ranged in price from $2.50 to $4; she let me get three or four pairs. In order to get the colors I wanted, I got shoes ranging from size seven to ten. I would stuff the bigger ones and squeeze my feet into the smaller ones. I really damaged my feet, but the most amazing thing was that my parents never put two and two together.

There’s this idea that those feelings don’t come up as an adult, but I still have to work against this primal instinct to have my shoes match my belt. My art is entirely still about those years of my life when things were color-coordinated and surfaces had to be perfect. Even if you go into a world that seems unconventional or radical, like the art world, there still are hierarchies and institutions of popularity. It doesn’t change, you have to change.”

All the Cool Girls Had One: 16 Women on Teen Status Symbols