Every young woman who moves to New York City arrives with a suitcase full of Zara and a head full of fantasies. These usually include an enormous Upper East Side apartment complete with a walk-in closet full of Manolo Blahniks for a mere $750 a month courtesy of Carrie Bradshaw, or consistent invitations to fabulous parties with Manhattan’s elite and a coveted relationship with the staff at Bergdorf Goodman thanks to Serena Van der Woodsen.
Every young woman except this one. Blame it on my study abroad experience in college or my Midwest upbringing, but I knew what moving away from home meant. Your friends and family living thousands of miles away doesn’t always lend itself to fancy parties and fancier shoes; instead nights are more commonly filled with dinners for one and the Zara clearance rack.
Don’t get me wrong, I was more than familiar with the iconic New York woman. The Rachels, the Carries, the Hollys and of course the Serenas. I had no idea what “73rd and Lex” meant, but I dreamed of confidently saying it in a cab. I fantasized of being recognized at Bergdorfs, but I mostly shopped at TJ Maxx. I loved their lives, yet I knew nothing about them.
It’s been a year since I moved, and every day, New York has been my personal tutor on the subject of Manhattan’s elite. Every morning a group of perfectly groomed, uniformed 6 year olds pass me on their way to private school, and every day busy men in expensive suits hustle down Park Ave. One of those six year olds has Kennedy blood, and one of those suits’ last name is older than this country. I sit next to them at brunch and on the subway. I’m in their world but not of it.
If status was the key to making it in this city, then I need to find a locksmith. Midwestern suburbia doesn’t scream “it girl”, but no one screams louder than Serena Van der Woodsen.
As they always say, if you can’t beat ’em, dress like ’em.
From there, I started making a list of the best Serena Van der Woodsen looks. I scoured Pinterest for inspiration photos and raked through my closest to see what I could recreate. I tried them all. From the casual yet sophisticated arrival in Grand Central outfit, Serena’s including brands like Ralph Lauren and Louis Vuitton, to the elegance at the White Party, I did my best to replicate Serena’s best looks. Maybe just maybe a little bit of that it girl magic would rub off on me.
The Grand Central Outfit
Arriving in Grand Central that morning, I almost felt like Serena, almost. Sure our circumstances were vastly different, Serena was arriving in Grand Central Station after mysteriously jetting off to boarding school without so much as texting her best friend, while I was hoping to catch the 6 train downtown on time, but I was hopeful. I could almost hear “Spotted…” in my head the whole time, but there were no tweens twittering about my arrival. Aside from the strange stares I always get from taking photos in public places, my existence remained pretty pedestrian.
Next up was the uniform. Despite the strict dress codes of New York City private schools, Upper East Side queens are known for bending the rules when it comes to fashion. Serena was the queen of disheveled chic. Loosened ties and untucked shirts went hand in hand with her tousled hair.
If Serena and I had anything in common, it was messy hair. While hers passed for effortless, mine was usually mistaken for unbrushed. I could do the grunge look, but could I do it as well as Serena?
The Brunch Outfit
Next was arguably the most important Manhattan woman’s wardrobe staple, the brunch outfit. Serena never was shy about color. Regardless of the occasion, she touted bright oranges and blues in tons of her onscreen outfits. Strutting around in this get up, I felt as close as you could to Upper East Side royalty…that is until my feet started bleeding.
As extra as I am, 3 1/2 inch heels aren’t typical of my normal brunch attire. Faced with my bloodied heel, I figured it was time to head home. I was too poor to hail a cab much less hail a cab to Brooklyn, so I prayed for an empty seat on the L train.
This time, I know I was noticed, but it had more to do with my limping down Broadway than my fabulous outfit.
The White Party Dress
No loyal Gossip Girl fan could forget the White Party. A group of designer clad high schoolers partying together at a million dollar Hamptons estate, a reality that could only exist in Manhattan. Everyone remembers Serena looking effortlessly chic per usual in her Oscar de la Renta gown.
I didn’t have a Hamptons party to crash, but I did have the streets of New York. People didn’t buy the it-girl vibe I was selling. Believe it or not, a white gown on a weekday in Washington Square Park reads a little more runaway than runway.
The Casual Coat
This was the easiest look to recreate. Most women own a black fall coat and a chunky knit scarf. However, when I searched for the most iconic Serena outfits, this always popped up. What exactly was it about this outfit that made it special? Could the answer be as simple as the girl wearing it? If so, I wasn’t sure I was the girl for the job.
The Party Look
Serena is shown here dressed up for a fabulous event. I am shown here dressed up for work. Enough said.
The Photoshoot with Blair
In this episode, Serena and Blair steal the clothes from Eleanor Waldorf’s (a famous New York fashion designer, naturally) new collection and hold an impromptu photoshoot all over Midtown Manhattan. If you weren’t jealous of their lives before, this episode will do you in. Maybe it was the culmination dressing like Serena for a week or maybe it was the DVF headscarf, but this was the first time I started to feel a little unlike myself but not in the way I imagined.
When I walked to the subway, headscarf tied around my ponytail and cocktail dress fitted like a glove, I wondered what the people on the street were thinking of me. After all these outfits, I didn’t feel more like an it girl, I feel more like someone pretending to be an it girl.
I walked back to my apartment from the subway, leaving the stares and the city behind me.
When I made it back to apartment, I took a look at my closet. The absence of labels glared at me harder than ever. Despite my efforts, I couldn’t help feeling like a Dorota in Waldorf’s clothing. No matter how much I dressed up my discounted wardrobe, I was still a polyester blend and she was still a mulberry silk. She had a voice that sounded like money, while I was stuck staring at a green light.
As I took off my discount heels, bloodied from my post brunch walk to the subway, I took a good look. They may not be Manolos, but they were mine.