The Power of Red Lipstick
I have a vivid memory of being six years old and up too late in our old house. My parents could never get me to go to sleep, and we didn’t have cable, so I’d be up all night watching shows like Soul Train and Night Flight. And one night on Night Flight I saw the video for the Eurythmics “Sweet Dreams Are Made Of This.” I saw Annie Lennox, in her suit, with her bright hair, with her dark eyeliner, with her red lips. I saw her and all I could think was I want that.

My first experience with makeup was in an old sewing kit my mother gave me to play with. It was full of her old makeup: shimmering powder blue eyeshadow, bright coral lipsticks, bright pink blushes. All from the 70s, before she had children, and, in retrospect, loaded with extremely vintage bacteria. Maybe that case of pinkeye I got in kindergarten wasn’t from the nap mats, after all.
I put on that makeup to play with friends, wobbling in mom’s high heels and playing at adulthood as so many of us do. Wearing that makeup, either mom’s old stuff or the little sparkly things sold to little girls in the 1980s at drugstores, once to school only got me yelled at by a teacher. Along with my friends who joined me in getting tiny tot tarted up at recess, I was brought in front of the classroom and my painted face was pointed out as ridiculous. It was probably the first time I heard the word ‘hussy,’ before we were sent to the bathroom to wash our faces.
Outside of that, though, I was something of a tomboy. I was the only girl in my class with short hair, and my major style inspiration as a 7-year-old was Wil Wheaton in Stand By Me. I grew up in a log cabin in the middle of five acres of forest land, where getting covered in ticks and chiggers romping through the trees (or playing video games in the basement) were more the order of the day than pretending to be a princess. The ‘dress-up drawer,’ full of more of my mom’s random castoffs from the 70s, and the makeup just came out just when other girls came over to play.
When puberty began its attack on me at the tender age of ten, leaving me the most curvaceous and menstruating girl in the fourth grade, I had only one defense: to become Not Like Other Girls. From tweenhood on, that became my stance: wearing makeup every day was for girls who cared too much about what people thought about them. I was fine in my men’s pants and occasionally slapping on some eyeliner for spooky goth reasons or the occasional formal obligation. I’d be the one rolling my eyes with male friends as we waited for the girls to get their faces put on before a night out. Dames, right? As long as my zits were mostly concealed, what did I care about putting anything on my face?
I didn’t want to be girly, that was the heart of it. I so much so didn’t want to be girly that for a time in my teens and twenties, I put serious consideration into transitioning. It would really make me not like the other girls, if I wasn’t a girl at all. I never made that leap, though, for all kinds of reasons; one of them was the memory of being that little girl happily playing in her mom’s makeup box. I couldn’t possibly actually be male inside if there was some part of me that got a little thrill from reading eyeliner tips in Seventeen, or if I actually did like the way I looked when I got all done up.
That was just society telling me that, of course. Society likes to tell you all sorts of things. Shave your legs? You’re part of the machine. Spend time blow-drying your hair? Yeah, you’re welcome, patriarchy. And spending twenty minutes getting your eyeliner wings perfect? You’re basically just a helpless pawn who only cares about satisfying the male gaze, and worse yet, you probably don’t even realize it. If only! I thought. If only more women could be like me and not do any of that nonsense. If only they realized how superior it was to not care.
It took a long time for me to realize that my not caring was really just not listening. In my quest to not be girly, I’d only really succeeded in shutting out the voices of other women. And more importantly, and more damagingly, I didn’t hear the voices of people like me. People who felt too boyish to be a girl, and too girly to be a boy. When I thought I hadn’t been caring, I’d really been desperately caring, looking for a side where I would fit. And when I couldn’t find a hole for my circular-squarish peg to fit into, all that did was make me hate myself.
It was everyone’s dearest friend, the Internet, that finally blasted my un-madeup eyes open to a new world of things. For all that Tumblr is a mess of animated gifs and teenagers yelling at each other, it exposed me to important new voices. I learned there were other people like me, people who felt in some muddled mid-space between the polar ends of gender, queering up the binary. I learned I was not alone, and more importantly, I learned it was okay to feel that way. I didn’t have to choose a team. I could make my own team.
And after I’d learned that, I learned about a whole world of women who loved makeup, but not because it made men want to fuck them; they loved it because it made them feel beautiful, feel strong, feel like walking, breathing pieces of art. For the first time in my life I started to see makeup as what it really can be: an art form, one that can require skill and dedication. I didn’t roll my eyes when I watched a friend spend an hour putting on her face before we went out anymore. I saw that she was building something there, that she was working a magic. She was casting a spell that gave her armor, and gave her power.
I didn’t have that power myself, not yet. I’d slowly been muddling my way towards finding a way to love myself. I’d been fat my whole adult life, and I’d just started to accept that it was okay to be that; I didn’t have to keep torturing myself towards some image of thin that I’d never reach. Part of hating my fatness was that I hated my clothing and had nothing I felt comfortable in, nothing that made me feel I looked good. I just wore what fit. I kept my hair long because I thought cutting it short would make me seem too boyish, too butch, all unacceptable for whatever adult world I thought I lived in.
Then, after a span of six weeks where I had to find a new apartment, move into a new apartment, and turn thirty, I let out a grand and tremendous FUCK IT to the universe. I cut my hair boy-short and bleached it until it was the color of a newborn chick. I found the one article of clothing I thought I looked good in — raglan-style baseball shirts — and bought one in every color I could find. And funny, how it happened, but once I did these things that made me feel like I looked good, I actually felt good. And other people started telling me I looked good, too. (For all that self-love is the most important, it sure as hell does feel good to get outside confirmation.)
I felt good, but something still didn’t feel quite right. I looked more boyish than ever, even though I felt more aligned with my female identity than I ever had before, just out of feminist solidarity and sisterhood. There was still a missing piece.
I remembered Annie Lennox. Then I bought my first red lipstick.
I spent half an hour agonizing over different tubes in the drug store. I wanted something stoplight red, something candy apple red, something bitch red. I wanted something unmistakable on my face, nothing nude or natural or possible to overlook. That night I bought a $7 tube of Revlon, a thing of Old Spice deodorant, and a box of wine. I looked at those purchases on my counter and felt like I was staring at the spell components to summon up my true form.

The drugstore lipstick didn’t have the power I wanted, so I turned to my friends on the internet. I had surrounded myself with a cosmetics coven of women, Sephora queens who were absolutely hungry to get their beautifully painted nails into me and bring me into the fold. They pointed me to brands and shades and before I knew it, my credit card was out and a box arrived on my desk a few days later.
The first red lipstick I loved was in the color ‘Vesuvio.’ Bright red like schoolhouse bricks, and wearing it made me feel explosive. I’ve worked in the same office for over ten years, and when I walked into work with bright red lips, everyone had something to say. “Wow,” was a popular comment, along with “what’s the occasion?” It’s nothing special, I told them. Just a thing I’m trying out.
Once I started trying it out, I had no interest in stopping. Adding that extra minute of painting my lips in the morning gave me this moment of almost meditation in the bathroom mirror. This is your face, I would think as I traced the edges of my mouth with a liner. This is who you are. You exist in this world, and people will see you.
Because people did start seeing me more, once I began wearing red lipstick every day. I caught extra glances towards me on the subway, got compliments from grocery store clerks, and once had a man yell from his car at me, “RED LIPS!” Now, street harassment is almost never a complimentary thing, but in that moment I had to laugh. Just one little thing and I was almost stopping traffic.
Yes, I was getting more attention from men, but I didn’t care. Kissing boys when you’re wearing red lipstick just means you both end up smudged. I loved it for the attention it made me give myself. I gathered a collection of different shades of red, all with names that felt like weapons, like armor, like noble titles. Cruella, Dragon Girl, Fire Down Below, Dressed to Kill. There’s a line of lipsticks I’ve had my eye on all named for women, the colors of Greta, Lana, Rita, Marlene, and more. If they had an Annie, that’d be the first I’d buy.
One morning, when I was up at 5 AM in order to take a cross-country flight, I thought to myself, maybe I won’t wear lipstick to the airport at 5 AM. And then I thought, no. No, there is no better time to wear lipstick than going to the airport at 5 AM. In that one extra minute I’ve put on my armor to face the indignities of whatever the day will hold. I’ve done one damn thing to show myself I think I’m worth the trouble.
There’s an ad for Kate Spade (which I’m still not girly enough to know exactly what that is — purses, maybe?) that several of the people I know have sent me because it reminds them of me. “She has a way with words, red lipstick, and making an entrance.” I always had the first of those; adding the second absolutely brought me to the third.
Red lipstick’s become a part of who I am, now, but I’m still me. Still butch-ly coiffed and dressed, still a bit of a tomboy, but now just a little girly. Just enough to be strong, because girls are strong. Just enough to bring that sense that I’m at play every day.

Originally published in Mathom House.