Sophie Henry

When I was 12, I asked my mom if I could start wearing makeup, if I could buy some mascara. She almost burst into tears at that moment out of pure relief, and perhaps a little bit of excitement. Prior to that day, I had been deep into my tomboy phase where I put all my focus into schoolwork and nothing into my appearance. Well, maybe not nothing. I did have to put the work into putting my hair into a ponytail every day and gelling down the front — any photos of me in the sixth grade are almost too cringy to look at now.

I honestly don’t remember my exact reasoning behind wearing khaki shorts and a dog tag to school every day that year, but I do remember feeling ugly. I remember feeling like I didn’t belong, like the other girls and me were two different species. And my tomboyishness certainly didn’t help alleviate these feelings. In my mind, I simply didn’t have the time or the need to shave my legs or tame my frizzy hair — a symptom of the Floridian humidity. Making myself a tomboy seemed like the best option. No fuss meant more focus, and more focus meant better work habits. What more could a mom ask for?

Yet, I knew my mom secretly wished I would grow out of this phase. I know she dreamed of going to the mall with me solely for the purposes of window shopping. Or of spending hours flipping through sales racks to find the best deal. Or of helping me do my makeup for senior prom — which never ended up happening anyways. 

So, on that day when I asked her if I could buy mascara, she was positively ecstatic. She asked me no questions, afraid I might change my mind. Together we went to the grocery store and walked down the aisle with the makeup section, a place I had never before dared to go. I remember thinking the options were endless — little did I know what Sephora was at that time. My mom convinced me to buy the ultimate beginner’s mascara: Maybelline Great Lash. Black, not clear. If I was going to start wearing makeup, I wanted it to be noticed.

This was around the time when some of my classmates began to have their bar and bat mitzvahs. Usually, everyone would skip the ceremony and show up when the party began — a party that involved wearing a dress, a concept that was drastically unfamiliar to me as of late. For the first bar mitzvah I attended, I tried to flat iron my hair — I did a pretty terrible job — put on a black dress and applied some mascara. My classmates were jaw-droppingly shocked. I don’t want to admit it, but I kind of liked shocking them. I kind of liked the way I looked that night and the way people looked at me. And so, my makeup escapades began. 

At first, it was just mascara. Then, flat-ironing my hair became a staple in my life — a time-consuming one at that — as a remedy for my eternally untamed hair. Shortly into seventh grade, I made a new friend who had a penchant for eyeliner. The way that I’m writing this makes it seem like I had traded a tomboy phase for a goth one — that wasn’t the case at all. I looked more or less natural — at the time, wearing a little makeup just felt like an excessive amount of makeup. I did, however, look completely different, in the sense that I began to embrace the tropes of femininity. I began wearing skirts, styling my hair down and putting on makeup every day.

But the main effect that makeup had on me that year was internal. What I didn’t know at the time was that wearing makeup so routinely would make me dependent on it, not just for functioning, but even for a modicum of confidence. It would take me years from that point to regain the confidence that I had in myself as a kid who didn’t have a care in the world.

It started with eye makeup, but as teenage acne started to set in — and mine was consistently bad — thus began my coverup days. Foundation and concealer became my two closest acquaintances. They weren’t miracle workers, but they did a fairly good job of hiding my acne-riddled skin from my classmates and friends, and family. I tried various treatments to improve my skin, including topical creams, antibiotics, and even a few rounds of microabrasion used for acne. By the time I reached ninth grade, I was fully addicted to the routine of covering up my skin. Each morning I would find myself frantic and running late because I had spent so much time putting on my makeup. And the worst part is that I hated it. I hated all of it. I hated wasting all that time, putting it on my face, feeling like a different person, and having it melt off my face in the Florida sun. I wanted to just roll out of bed and go to school unconcerned with my appearance — or how other people judged my appearance. But people began to compliment me, and this created unwanted expectations — at least my teenage mind thought so. Once people perceived me a certain way, I wanted it to stay that way, no matter the cost.

Over the years, the costs exacerbated. Makeup first took away my time, then it started siphoning my confidence, the opposite of what makeup is often advertised to do. I can recall only one day in all of high school when I didn’t wear a full face of makeup. I began to hate the way I looked both with makeup and without it. I told myself that it was normal to be experiencing these high school years of discomfort, and it was. But that didn’t make it any less painful and internally taxing. And it didn’t make me any more sure of myself.

There was one time in senior year when not even a full face of makeup could give me an ounce of the self-assurance I so desperately desired. I was at a choral conference in Tampa with some of my classmates, which should have been a highlight of my final year in high school. Instead, all I can remember is crying myself to sleep at night in a hotel room. This guy who I had known for almost my entire life was also at the conference — and who I had also really liked since eighth grade. We ended up going to different high schools, so choral functions were really the only times we ever saw each other. But when he invited me to meet up on the last evening of the conference, I said no. Only because I was too embarrassed by my skin and too disheartened to attempt to cover it all up. Who knows what could have been?

I wish I had been more confident in my true self. My relationship with makeup would have been much less toxic. I relied on it to make myself feel worthy, when in the end, it only made me feel worthless. I wish I had had an epiphany that allowed me to conquer the need to hide my imperfections. I wish I realized that nobody cared. It took me forever to realize that, even though I thought everyone was always judging me, they were really just stuck inside their own heads, worrying about themselves. 

When the pandemic happened, I suddenly stopped wearing makeup altogether — didn’t everyone? Online classes relieved me of the need to apply makeup and put on a brave face every morning. And after a while, my skin improved to a manageable level, so much to the point where when the world opened back up, my dependence on makeup was close to none. It was liberating. Today, I can be just as confident and carefree wearing no makeup at all, as I often do. With everything going on in my busy college life, it doesn’t even warrant the 100th spot on my to-do list.

Everyone has imperfections, but ultimately, it’s a matter of how strong you are, of how resilient your confidence and willpower are. It’s okay to be imperfect, just as long as you can love yourself regardless. Don’t wear makeup to hide yourself. Don’t wear it to impress someone else. And definitely don’t wear it because you feel like you have to. It’s your choice, in the end. Just make sure that your confidence comes from within and not from the products you don’t want to do without.

Jacqueline Kaskel edits for the WKND desk. She is a junior in Branford College majoring in English Language and Literature.