I Gave Myself The 90s Rom-Com Makeover I’ve Always Wanted
Will I feel hotter? Will people treat me differently? Will I land the date of my dreams only to find out it’s been a bet all along?
We all know how this story goes: homely nerd girl with paint-splattered overalls is a high school nobody. Then one day someone more popular and attractive graciously takes her under their wing. A makeover montage set to a catchy pop tune ensues. She takes off her glasses, lets down her hair and suddenly this ugly duckling is now super-babe Rachael Leigh Cook.
As a 25-year-old sophisticated adult with a brain, I now see this trope is not only highly unrealistic, but also problematic in the way it links a woman’s value to her physical appearance. But having grown up with makeover rom-coms like “She’s All That,” “Clueless” and “The Princess Diaries,” their narratives sank into my pubescent brain and?—?whether I’d like to admit it or not?—?shaped the way I saw feminine beauty. To this day, I still have a habit of lumping women into “hot girls” and “normal girls,” with my self-image planted firmly in the latter group.
In case you’re an alien from another planet, here’s what I’m talking about:
That’s not to say I think I’m some hideous schlub. But I’d be lying if I said I didn’t spend a good chunk of high school waiting for someone else to realize I was beautiful. I mean, haven’t we all dreamed of someone seeing through our defensive bullshit and saying hey, you’re actually the princess of the fictional nation of Genovia? A small part of me has been waiting for that moment since childhood.
Now that I’m a grown-up adult woman, I’m not going to wait around for someone else to realize I’m secretly a mega-babe. I’m going to go out there and give myself that rom-com makeover moment I’ve embarrassingly fantasized about since 1997. Sorry, Freddie Prinze Jr.!
Here’s the plan: I’m gonna take off my glasses. Brush my hair. Wear a real bra and makeup and maybe some heels (omg please no), ending with a full-on evening gown makeover. Will I feel hotter? Will people treat me differently? Will I land the date of my dreams only to find out it’s been a bet all along? Stay tuned.
Ok, so you might be wondering where I am on the “before” scale from Anne Hathaway’s frizzy-haired Mia Thermopolis to Julia Roberts’ “Pretty Woman” Vivian Ward. While we should avoid rating a woman’s looks, it’s safe to say my current style is unironically similar to pre-makeover Laney Boggs from “She’s All That.” Glasses (always), overalls (occasionally), and a semi-permanent look of judgy side-eye.
Like most people, I use my clothes to tell people what I’m about before we even speak. And because I generally dislike talking to strangers, I’ve cultivated a look that says “no thank you, I’m good here.” Cardigans, sensible shoes and t-shirts with no distracting or offensive images that might be misconstrued as a conversation starter. Basic in the most basic sense of the term.
If you’re not convinced, here’s a sexy sneak peek of my head-turning wowee-look-at-her style. Aaa-OOO-ga!
Current Beauty Routine
My everyday makeup routine consists of tinted sunscreen (because I’m super afraid of skin cancer) and mascara (because I once read in Seventeen magazine that Britney Spears never leaves the house without it and I haven’t evolved since I was 15). Oh, and chapstick. Lots of chapstick. If I’m going on a date, I’ll spring for the tinted variety.
I’ve been a proud glasses girl since the 9th grade. Aside from the improved vision, I love the way they frame my face and give the optical illusion of symmetry. While I’ve changed frames many times over the years, my glasses have been more than just a beloved accessory—they’ve been a part of my face for more than a decade. I’m not especially thrilled to be giving them up for the week. But what kind of makeover would this be if I didn’t get to whip off my glasses and dramatically shake my hair around?
Minutes into my makeover, I feel hotter and blinder than ever. While many makeover movies feature life-long glasses girls, very few show the frustrating transition from wearing spectacles on your nose to jamming a foreign object into your eyeball. At least my girl Nia Vardalos from “My Big Fat Greek Wedding” knows the struggle.
^This continues for 30 minutes until contacts are installed in my face.
If I’ve learned anything from romantic comedies it’s that clothes. are. crucial. Now that I’m glasses free and ready to party, it’s time for a style transformation.
First stop: shopping the boutique of local designer Anastasia Chatzka, whose Barbie-meets-Betsy-Johnson stylings could have been wardrobe for any 90s rom-com. From bubblegum pink numbers to plaid minidresses befitting high school mean girls, each design allows me to test drive a different cliquish persona.
While none of the outfits really feel like “me,” I enjoy trying on the characters and imagining what the girl in the red pleather dress eats for breakfast. I even get a little sporty testing my golf swing when I put on plaid shorts reminiscent of the unitard Cher Horowitz wears to workout to Buns of Steel. And yes, I keep my socks on the whole time.
In the end, we decide on a couple outfits that make me feel like I could easily hang with the hot girls. Sit with us? As if, virgin!
Working in heels
I roll into the office feeling vulnerable in a short skirt, teetering on high heels. I’m suddenly super aware of having a vagina (what if I drop something?) and the limitations of my footwear (what if I need to outrun a bear?). I have the sense that everyone is looking at me, and not for my personality.
Aside from my heightened paranoia, there is an upside?—?I’m forced to sit up straighter in meetings (no more criss-cross applesauce) and my department presentation goes swimmingly. For once I feel like a grown-up who deserves to be taken seriously rather than three kids in a trench coat. Look out world, I’m wearing a dress!
BUT WHAT ABOUT THE PROM?
Ok, so I’m not going to prom, but I will be attending a fashion show at the end of the week and I gotta look the part.
We head next to Rent The Runway for some fashionable formalwear. Entering their Chicago store feels like walking into Blue Ivy’s personal dress-up closet. The lighting alone transforms me into an airbrushed cover model and I can’t help but rub my face on all the silky fabrics.
Behold, the full-on shopping montage you’ve all been waiting for:
Just as we’re heading out, our awesome stylist Rachel grabs me and says, “Wait, I have one more thing I think you’d look great in.”
As she pulls out a floor-length pink (!) number with an open back I’m thinking, “No. Nononono. The world does not need to see my thirteen-inch scoliosis surgery scar. And this attached scarf? Who am I, an old-timey Broadway star?” But after some hesitation, I bow to her expertise. And daaanng was she right! Somebody give me a tiara!
Hair & Makeup
Up until now this makeover has been all about my bod. And now my bod is like “hey, what about my face?” Eager to get my own “Princess Diaries” face reveal (don’t worry, it happens), we head to Blowout Junkie for some expert hair and makeup.
As a wash-n-go kind of gal, I’m pleased to get a few hot-girl hair secrets (apparently flipping your head over and wiggling around is not the best way to blow-dry). I definitely tip my newbie card when the stylist asks how I wear my bangs, I just say “in the front.”
Next comes the makeup artist, and man is she an artist. She paints a whole new face on top of my regular face! With just a few brushstrokes, my cheekbones are bronzed to look like I’m not afraid of the sun and my eyebrows are darkened to match my feminine mustache. Applying the false eyelashes is the worst part?—?it feels like getting a glaucoma test at the eye doctor?—?but I guess mild discomfort is beauty, or whatever they say.
Now the moment everyone (just me) has been waiting for. I’ve been poured into a gown, given a brand new face and my hair has been cajoled into “beach waves.” I feel very outside of my comfort zone, but unlike earlier in the week it’s not so…cringey. I’m fully inhabiting the role of “hot girl who gets invited to stuff.”
We roll up to Mario Tricoci’s Runway Rockstar fashion show and to my disappointment there is no grand staircase for me to slow-motion descend. There’s just a guy with a clipboard who does not seem terribly impressed by my fancy dress and Target heels from 2005 (my feet did not get a makeover). The open bar and frou-frou goodie bags do however confirm my suspicion that beautiful people are given free stuff all the time.
The show itself is mostly just a parade of butts and swingy black fabric, but I feel a special connection to the models when it’s announced that they too have undergone makeovers (my brethren!). As their families whoop it up in the audience, cheering on the models like it’s a Bear’s game, my heart swells with pride.
On the way home from the show, I run into a friend on the bus. I look so different she doesn’t even recognize me at first. Like, I have to say “hey, it’s me, Anna.” Does this mean the transformation is complete? I’d say so, except I’m still wearing my canvas backpack with an evening gown.
Before this makeover, it was easy for me to feel like the funny girl or the smart girl or the good friend (all qualities I’m very proud of), but I rarely felt like “the pretty girl.” In fact, the last time someone told me I was pretty I cried publicly at my coworker’s birthday party. But this makeover gave me the opportunity to play the game of conventional beauty on a level I never had before, to try on the prom queen identity and see for myself if it was as fulfilling as I had dreamed as a teenager.
While I wasn’t showered in gifts from secret admirers, I did get quite a few valuable takeaways from this week:
- I have an unfortunate habit of flaring my nostrils in photos.
- I’m more vain than I’d ever known. By the end of the week, my phone was FULL of selfies and I stopped to check my appearance in every reflective surface I passed.
- You can’t wear a sports bra with an evening gown. Like, don’t even try it.
- Gender is weird. This week, I felt much more aware of the fact that strangers were seeing me as a woman before they saw me as anything else. People called me miss, sweetie, and honey more than ever before in my life and it gave me the heebie-jeebies.
- Even hot babes have to do their jobs.
Perhaps the biggest takeaway though, is that I have the power to make changes for myself. Unlike all those romantic comedies I loved as a kid, no one was telling me what to wear or how to be cool. Sure, I took advice from professionals and tried styles I normally wouldn’t have, but at the end of the day I chose what went on my body and how I felt about it. I was my own beauty yardstick and ultimately, nothing else measured up to how I feel as my regular, glasses girl self.
All original photos and videos are courtesy of Dose’s Drew Wittler and Ryan Luciani. Original illustrations by Dose’s Ines Vuckovic.