How Embracing My Inner Tomboy Made Me a More Confident Person

These days, tomboys on TV are always cool. Max in Stranger Things is the girl every boy wants to be friends with. Casey from Atypical lands one of the cutest boys on the show (despite the fact that she’s more interested in girls). But, back in the late-’90s and early-2000s, when middle school was my worst enemy and I didn’t have relevant role models on TV, this was definitely not the case. 

When hoop earrings, tight jeans, miniskirts and camisole tops were a ticket to popularity, I rocked breakaway pants, T-shirts, Sauconys and a baseball cap. It turns out that “tomboy phase” of mine wasn’t really a phase after all. It was just something that I needed to practice and perfect in order to turn it into something I love about myself. But, of course, I didn’t know that as a kid.

I played with Cabbage Patch Kids and Barbies, but I also loved video games and climbing trees. The one thing I wasn’t willing to compromise on? My outfits. Dresses were a big no-no and anytime my mom tried to get me to wear something pink, I refused. I used to cry when I had to wear pantyhose and I preferred board shorts with a bikini top for a day at the beach.

Sometimes, when I didn’t like what was in my own closet, I raided my brother’s. I felt comfortable in his band T-shirts and flannels. But that didn’t mean I only wanted to wear boy’s clothes. I remember going to Old Navy with my mom and grandma and bringing a pair of boys’ carpenter jeans with me into the fitting room. Even though I liked the way the pants fit, and they definitely looked better than the frilly girls’ clothes hanging on the rack, the jeans still didn’t feel right. The thing is, I was still a girl and I wanted to be seen as a girl, but I just didn’t want to wear anything from the girls’ section.

When I went to sleep-away camp for the first time, the summer before fourth grade, I was one of the first ones in my bunk to wear a bra, which I obviously concealed beneath big T-shirts. Still, I could go from doing my hair with the girls to playing basketball with the boys. And, when it came time for the dance, a lot of boys were waiting to ask me out. Unfortunately, it turned out that liking a girl like me—a tomboy—was not socially acceptable. They began rescinding their offers. But I didn’t care. I was comfortable in my skin, and things stayed that way until I hit middle school and hurtful remarks were hurled my way.

In seventh grade, I went through a phase (this was actually a phase, I promise) where I had to wear at least one article of clothing with the New York Rangers symbol every single day. Naturally, a Rangers hat was my go-to. My friends tried to rip that hat off of me every chance they got, simultaneously pulling the barrette out of my hair. When we we're hanging out, these friends would also insist that I try on miniskirts and they’d “ooh” and “ahh,” remarking that I had an excellent figure. 

As time went on, I realized that if I wanted to fit in more, I had to find a way to blend these two sides of myself into one cohesive person. But I struggled to figure out which one I was. Was I more one than the other? It ended up being a lot of effort to figure that out. 

Finally, on the last day of eighth grade, I found my look. I wore a green skort, a white tank top and a matching Adidas green and white sweatband. I might have looked like a tennis player, but I was finally feeling like the truest version of myself.

As I moved on to high school, I found even more harmony with balancing my rougher tomboy side with the part of me that melted into a puddle around my crushes. I realized that it didn't matter what I wore because being a tomboy is not just about how you dress—it’s about how you feel. And I feel comfortable in clothing that doesn’t put my curves on display and I really, truly prefer jeans that are a bit baggy. 

Nowadays, I’m in a long-term relationship with my now fiancé, who liked me from the moment we reconnected in college, four years after our first meeting. We ran into each other at an activity on campus, and he remembers I was wearing a cute royal blue top (that I borrowed from my much trendier roommate). Of course, the next time I saw him, I was wearing jean shorts and a T-shirt, and it made no difference to him at all. Because he accepts me for who I am, whether I’m wearing a cute shirt one day or baggy shorts the next. He knows I feel most confident when I’m rocking my Keds instead of a pair of heels.

Now, years away from my middle school woes, I’ve learned that it’s OK to wear dresses and skirts, and even get my nails done from time to time. To be honest, I’m not sure when this acceptance happened. Maybe it emerged when the bullying stopped, or perhaps when I learned not to care what others thought. It might have been around the time when my peers learned the word “superficial” or the moment I realized I didn’t need to base my confidence on how I compared to other girls.

Essentially, I grew up and I grew out of caring what other people thought. At the end of the day there’s no pulling me away from my oversized T-shirts and hoodies, boyfriend jeans and Converse sneakers, an outfit that makes me feel much more in touch with my true self than a cocktail dress ever will.

But, speaking of dresses, these days there are a few hanging in my closet—you’ll just have to dig through the flannels to find them.