What My Constantly Changing Haircuts Taught Me About Being My Most Authentic Self

As I child of the 1990s, I experimented with some pretty cringe-worthy fashion trends, especially when it came to my hair. I overcrimped, oversprayed, and yes, overscrunch-ied. Overweight and insecure, I hoped if I dressed or did my makeup or styled my hair like the popular girls, I would miraculously bust out of my self-imposed cocoon and find myself transformed. I wanted to be like them — like beautiful, untouchable butterflies with their fair skin, high cheekbones, and voluminous, honey-colored curls cascading effortlessly in waves down their lean backs.

With my Italian-Portuguese heritage, I was the polar opposite of what I was desperate to emulate. I was olive-skinned, plump with a round face, and had dark, thin hair I loathed with a passion. I felt awkward and out of place. I was tired of standing out. I didn't want to be chubby, "tom boy Jen" with my glasses and dirt brown hair. I wanted to reinvent myself as feminine, sweet, blonde "girl-next-door Jen." The Summer before 8th grade I even had one of my friends drench my hair with a bottle of some mystery liquid that promised us golden, sun-kissed locks. The result: brittle, bleached hair that felt and looked like straw. I made a futile attempt to fit in, but instead ended up drawing more attention to myself.

Even after the bleaching fiasco of 1999, I continued to let my peers and my need for acceptance dictate who I was. I clearly wasn't going to be the all-American girl, so I decided to reinvent myself yet again. This time, I was going to be "rebellious Jen." I had a few friends from my hometown who were actual rebels, so I basically became a carbon copy of them. I went to a private high school and wore a uniform, so while I couldn't express my rebellion through fashion, I used hair and makeup. I would saturate my slightly wavy hair with hair gel, shellac it with hairspray until it was crunchy, and scrunch it up into greasy ringlets. I lined my eyes black, coated my lashes thick with mascara, and donned the biggest hoop earrings I could wear without getting myself into too much trouble.

Of course, I didn't look rebellious — I just looked like a teenager who didn't know how to apply eyeliner. The funny thing was, though, I convinced myself I wasn't doing this for everyone else. I told myself that my constant need to change my aesthetic was a form of self-expression. But that wasn't even close to the truth. I was trying to camouflage who I really was, because I wasn't ready to face it.

What I was hiding from wasn't on the exterior. I didn't realize it until I hit my second year of college and began the process of coming out as a lesbian to my friends and family. Finally being able to come to terms with what I wanted in my life was like a weight lifted off my shoulders. I wish I could tell you this revelation also prevented me from trying to fit a certain mold when it came to my clothes, makeup, and hair. Sure — I felt more confident in some ways, but mostly, I felt yet again, like an outsider. I instantly thought to myself that I didn't look the part as a lesbian. I wasn't gay enough. All of a sudden, the flowy, floral tops I wore and always loved looked too girlie. The makeup, which I spent hours meticulously applying, felt heavy and unnecessary. And my hair, which fell past my shoulders and down my back, felt like an anchor weighing me down and holding me back from living my new life as a lesbian in the city.

So, I made the biggest mistake of my entire life. I walked from my dorm to one of the cosmetology schools offering $10 haircuts and had the novice hair dresser chop my hair into what ended up looking like a mushroom cap. At that moment, despite the fact that I resembled a 12-year-old boy, I didn't feel like I'd regret my decision. In fact, I felt liberated. I was going to show the world who I was now — with my men's jeans, my minimalist makeup, and my short hair. This is how I was supposed to look right? I was sure of it. But it still didn't feel right. I could tell my friends, while supportive of my coming out, couldn't understand why I felt the need to change my appearance. When I went to gay bars and attempted to talk to women, I sensed they also didn't buy my cool and casual sporty look as authentic. I didn't feel like a freak or an outcast like I used to, but instead, something far worse. I felt like an imposter. In my distorted mind, it was as if the haircut was supposed to have this magical power of transforming me into some superlesbian. Instead, it represented yet again my own insecurities and my profound need for a sense of belonging.

It's been nearly 10 years since the "anything-but-super bowl cut" (as I've affectionately named it) of 2007, and I've learned a hell of a lot when it comes to my hair and myself. Practically speaking, I realized investing in a hairstylist you know and trust when making any drastic change is always a good idea. But there is a bigger moral to this story.

I've realized that a person can reinvent themselves a dozen times, but the most beautiful version of yourself is the authentic version. Every time I tried on a different persona or listened to other people's opinions on how I should look, it was like I was trying to squeeze myself into a box that just didn't fit. I felt trapped and alone, but I didn't know how to be myself. How could I know? I spent most of my life letting other people decide for me. But life is so much richer — so much more vibrant — when you choose to be you. I can be a lesbian and still decorate myself with the ornate necklaces and crimson lipstick I love. I can let my hair flow down my back or chop it into a pixie cut if I want to. I can wear sweatpants or a freaking wedding dress. I don't have to worry about being accepted, because I accept myself. If you've always wanted to dye your hair blue, rock hair extensions, or shave your head, do it. If you actually hate the idea of primping and curling and straightening, then stop it. Whether you want to stand out, blend in, or chill somewhere in the middle, just remember this: do what makes you feel like YOU.