1 Woman Wore a Halloween Costume IRL, and This Is What She Learned

POPSUGAR Photography | Mark Doyle
POPSUGAR Photography | Mark Doyle

Halloween is the one day each year that beauty girls are free to truly go HAM with their creativity. For years, I took the holiday pretty seriously. I had my mom help me with red lipstick in elementary school when I wanted to be a vampire. In college, I turned some weave into a Lady Gaga-style hairbow. In 2011, I sat on my sink to get as close to my mirror as possible to create that intricate eyeliner from Black Swan. But since then, I haven't participated in Halloween.

Maybe it's the fact that I am "adulting" in the real world and am exhausted by the thought of staying out late that has caused me to skip the day. But even though I haven't gone out in costume in four years, I've missed it. I was a performer in college, and Halloween was the last outlet left in my life to appropriately let out my inner freak. So when the opportunity to parade around NYC in full costume came up, I felt like I owed it to myself to say yes.

I decided that going for a retro grayscale-inspired style would be the most head-turning look (while still allowing me to feel like myself with lipstick and lashes). Full confession — I did not have the transformation skills for this, so talented Madison Personette of The Body of Art bravely took on the makeup challenge.

Right before it was go-time, I got cold feet. I'll admit, after my experience transforming my lips into Kylie Jenner's, I was wary of making myself look ridiculous for the world to see. So as a security blanket of sorts, I asked my friend Nick Maslow to join me on a Halloween beauty adventure, ensuring I wouldn't be alone on the journey. Here's what I learned from wearing a costume on a random day in August.

POPSUGAR Photography / Mark Doyle

Preparation Is Everything

With any major costume, you’ll want to do your research. With a grayscale costume in particular, you want to make sure that your outfit — and beauty — is perfectly black and white so it doesn’t throw off the whole look. I found the perfect vintage-inspired dress at Modcloth, wore a black wig to hide my light brown hair, and acquired long gloves so I wouldn’t have to paint my fingers . . . or ruin everything I touched.

While I provided Madison with some reference photos, she said that in the end, she used Pleasantville as her main source of inspiration. I also had initially prepared to wear sheer black tights, but Madison told me painting my legs would look way better. I trusted her instinct, and she was so right.

POPSUGAR Photography / Mark Doyle

EVERYONE Is Looking

This should seem like a given, but I honestly wasn’t prepared for the level of staring that we received. We started our journey on the subway, and fellow train passengers immediately gave us a wide berth when we boarded. (I can’t blame them — they were probably waiting for us to break into song and dance.)

At first, many people refused to make eye contact when we caught them looking. Eventually, because there were two of us and a photographer, observers could tell that we were part of some sort of project instead of especially . . . interesting citizens of NYC. Many approached us asking to take pictures, asking us what we were. When we were in Central Park, a man walking past stared at us for so long that he tripped and fell.

POPSUGAR Photography / Mark Doyle

POPSUGAR Photography / Mark Doyle

POPSUGAR Photography / Mark Doyle

You Will Feel Like a Freak — and Love It

As we paused to take photos in Grand Central, we caused a legitimate scene. There was such a large crowd surrounding us taking pictures that Nick whispered to me, "we should have a tip jar." Any initial reservations I had about rocking Halloween in real life vanished, and I started playing into my character. I broke out a few robot dance moves, posed like a retro movie star, and winked at passersby.

Sure, there was the occasional "What the f*ck?!" from pedestrians, but the positive reactions outweighed the negative ones. My heart melted when a little boy approached me, completely entranced, and his mom asked if he could take his photo with us. I was practically ready to quit my day job and become a performer in Times Square or be a professional princess for birthday parties.

I didn’t even bother trying to take off the makeup before heading home, which means I rocked face makeup on public transportation. While we’d experienced friendly New Yorkers as a duo, going grayscale solo yielded more awkwardness. No one would look me in the eye except my bus driver, who said, "should I even ask?" as I climbed aboard. "Just another day at the office!" I chirped.

POPSUGAR Photography / Mark Doyle

POPSUGAR Photography / Mark Doyle

Taking Off the Costume Is Difficult

I left the makeup on for a few hours after I got home not only because I loved the way it looked, but because I knew removal would be a daunting task. Once I got home, I used three face wipes before giving up and hopping in the shower. Water failed to even remotely budge my body paint, so I moved onto a soapy washcloth, which also didn't work. I eventually had to go over each body part three times with an old shower pouf, and even then I was still finding paint in random places. I also dealt with a few breakouts a few weeks later, so I must not have been as thorough as I thought.

POPSUGAR Photography / Mark Doyle

You’ll Feel Empowered

The most surprising thing about a dramatic costume like this is instead of you wearing it, the look wears you — and I fell in love with the feeling. While this may not be ideal in fashion, it is absolutely perfect for Halloween. Many friends would not describe me as a shy person, yet I am a self-conscious person . . . but when I wore this costume, I felt impossibly confident.

It’s a hard lesson to ingrain myself with, but it made me realize that taking risks and trying new things are not bad things. In New York City, everyone’s seen it all, so go ahead and wear green lipstick to work or contour your cleavage for a date.

POPSUGAR Photography / Mark Doyle

You’ll Rediscover Your Love of Makeup (and Halloween)

It’s pretty obvious that some serious skill went into this look, and seeing Madison work made me want to hone my own techniques. After years of being afraid to dabble in airbrush makeup, I recently started working with the Temptu Air. I have been hoarding fake lashes to wear them in my real life.

Above all, I was reminded of how truly fun Halloween is. Sometimes it’s nice to be a different person for a day! And thanks to this project, I’m planning on transforming into my generation’s ultimate beauty queen — Kim Kardashian — on October 31.

POPSUGAR Photography / Mark Doyle