Like many women, most of my middle school and high school fashion experience is peppered with memories of the things I thought I couldn't wear. I thought I couldn't dress like Lauren Conrad and Lo from The Hills because I was too tall. In middle school, I assumed I couldn't dress like Lizzie McGuire because I was too big. I was right about one thing: Choosing what to wear as a teenager is awkward (and often painful) as hell. For every celebrity I admired, there was a conversation in the back of my head about why I couldn't dress like them. I think of those conversations now and, like so many women feel about time we wasted hating our bodies, I'm a little sad. But it also makes me wonder what it would be like for women to wear those "off-limits" trends from high school today as adults.
While there are still a lot of silly fashion "rules" prevalent in society today, for myself and many other women, there is also much more freedom when it comes to how we feel about dressing our bodies. More and more people are realizing that these rules about what's appropriate versus inappropriate to wear are bogus, and that there's no one way to "dress for your body."
With the help of makeup artist Elisa Flowers and hair stylist Jinn, we transformed five real women into their high school fashion icons, styling them in all the outfits they never thought they could pull off — from sky high heels to a curve-hugging dress to a Juicy Couture tracksuit. The results are women full of confidence and joy, and are all the proof you'll ever need that every fashion trend is for every person who wants to rock it, no matter what.
Brooke dealt with body image issues growing up — and Mariah Carey's attitude is exactly what she wished she had had as a teenager.
"I love how over the top and glamorous Mariah's always been. She's the kind of woman that would wear a sequined ball gown to a cookout and not feel out of place. That was the level of confidence I aspired to have as a teenager," Brooke says.
"I struggled with body image a great deal in my youth. I put forth faux confidence, but deep down I was very unhappy. I was frequently told that I shouldn't show my legs or stomach," Brooke tells me. "This Mariah look allowed me to do both."
Brooke says that while the experiencing of was intimidating at first as her first ever photoshoot showing her stomach, it was rewarding in the end.
"I let fear keep me from enjoying something so simple for so long," Brooke says of rocking the Mariah-inspired look.
Buffy The Vampire Slayer
Tanya grew up in coastal California. "Think Laguna Beach meets The O.C.," she tells me. After skipping two grades, Tanya was the youngest of her peers by a couple years, a self-described "nerdy kid" who had trouble fitting in. Feeling a little out of place in school, Tanya found herself admiring Sarah Michelle Gellar as the titular heroine of Buffy the Vampire Slayer.
"I think I wanted to emulate Buffy in so many ways personality-wise that I ended up coveting her style more than I would have if I didn't admire her strength and fearlessness as much as I did," Tanya says.
While Tanya says she did try to copy Buffy's style every now and then as a teenager, she opted for safer options like wide-leg black pants and leather boots.
"I didn't have the confidence about my body that I do today, and wearing leather pants would have totally scared me into refusing to leave my parents' car when they dropped me off at school," Tanya explains.
Tanya says she was nervous to put on the leather pants and transform into Buffy, but the experience ended up making her feel powerful in a way she didn't expect.
"I genuinely thought it would be terrifying. But once I got into the outfit, I started to feel stronger. And then when I got those crazy high boots (somehow) on my feet, I felt like a slayer myself. The strength of Buffy is wild," Tanya tells me. "I just wished 14-year-old me could see what I was doing now. I think she'd be so proud."
Ana tells me she grew up as one of the largest and tallest girls in her class, which made her feel constantly self-conscious whenever she had to choose what to wear. As her body changed, she says she not only had trouble finding clothes that fit her well, but she second-guessed what she could and couldn't pull off as a plus-size teen.
"Even though we wore uniforms, outside of school or whenever we could wear regular clothing to school, I always dreaded it and placed pressure on myself to look good, and in my mind, I rarely did," Ana says. "Dealing with your body changing when it was already majorly different from your friends was something I struggled with all my childhood and in my teen years too."
Ana says that J.Lo embodied the attitude she wishes she had had as a teen whose typical outfit was "an oversized tee and basketball shorts."
"Jennifer Lopez was willing to take major fashion risks and she pulled it off by exuding the confidence I desired to have. She carried an attitude that screamed 'I’m beautiful and sexy and I know I look good,'" Ana tells me. "I remember always wanting to wear a full velour tracksuit but never feeling comfortable to pull it off. It was a personal victory for my teenage self walking onto set in that pink tracksuit."
While Ana says she felt more nervous during the shoot than she expected, retracting into her "teenage doubts," the environment on set made her feel amazing.
"The music blasting and the hair and makeup supplied me with the boost of confidence I needed to take on this amazing transformation and embody J.Lo," Ana says.
Like a lot of us, Sarah came to love the Spice Girls in the '90s, when she was in elementary school. But she remained a fan of the band, and one particular member's sense of stlye, into high school.
"Ginger in particular, through her style, always conveyed a confidence that I admired. She wore the most wildly revealing outfits while being completely comfortable in her body and totally seeming like a girl you’d want to be friends with," Sarah tells me. "Ginger came across as a leader, which has always resonated with me"
"I’ve never felt I had the curves or confidence to pull off any of Ginger’s outfits — even when my girlfriends and I went as the Spice Girls for Halloween," Sarah says.
Even if balancing in the heels proved to be a little challenging, Sarah says that the gorgeous dress and fun set helped her enjoy the moment and truly embrace the confidence of Ginger.
"I was so nervous and didn’t know what to expect going into the shoot, but knowing that I was representing Ginger imbued me with a sense of confidence," she tells me.
Mary J. Blige
Growing up as a "chubby teen," Patricia tells me that she believed there were only certain types of outfits she could wear.
"Nothing flashy, nothing tightly fitted, nothing bold, nothing colored, nothing creative," she says. "I was raised to believe that my chubby body could only be acceptable in simple, plain clothing that camouflaged my body."
Mary J. Blige represented a powerful presence to Patricia as a teen. Her music spoke to her, but so did what she represented.
"As a teen, I admired the way she handled in her songs what were tough issues then (like, finding love, being happy); her songs spoke to my teenaged-angsty feelings," Patricia says. "I also loved how she represented for the everyday girls in the 'hood, who were glamorous in their own way, and not in the way that pop culture dictated 'glamour' at the time."
For Patricia at the time, big, in-your-face outfits that took up space — things like a giant fur coat, or head-to-toe leopard print — were not looks that fit in with the aesthetic that her teen self was "allowed" to wear.
"Mary carried herself in a way I did not think was available to me," she says. "She was so fabulous and I did not believe I could ever be that fabulous."
As Patricia was transformed into the very version of Mary J. Blige that she used to think she couldn't be — big white coat, giant fur hat — she tells me she felt "released" from the belief that her body was only appropriate in certain types of clothing.
"It's a belief that became crystallized as a teenager and one that I've been chipping away at for years. When rocking that amazingly fabulous fur I felt like my body was being honored by something so glamorous and rich and it affirmed that I am amazing," Patricia says. "I wish I could take a piece of this experience and give the feeling to 15-year-old me. Thirty-five-year-old me is tremendously grateful to have accessed this blissful, body-affirming feeling. I still carry it with me."
This feeling that Patricia mentions is something that is important for every woman to find in their own lives, in whatever way possible — and it doesn't necessarily require a giant fur coat or a Juicy Couture tracksuit, either. This simple reminder to our 15-year-old selves (or our 35-year-old selves, or our 70-year-old selves) that we and our bodies are worthy of wearing whatever we want is necessary and life-affirming. And the more we find opportunities to tell ourselves that, the better.
Hair: Jinn Hair using Davnines
Makeup: Elisa Flowers at BA-Reps using Make Up Forever
Bustle Team: Deputy Editor, Fashion & Beauty: Kara McGrath; Senior Fashion Market Editor: Gabrielle Prescod; Fashion & Beauty Editor: Olivia Muenter; Booking/Production Manager: Guillermo Perez; Art Director: Bry Crasch; Junior Art Director: Brit Phillips