Why I Chose To Rock Red Lippie For The First Time

As someone who's as pale as a piece of printer paper, people have always told me one thing regarding my makeup application habits: Dark and vibrant colors aren't for me. Until recently, I listened to them. When it came to wearing red lipstick for the first time, especially, I hesitated to take the plunge.

For most of my life, women at makeup counters have handed me pale blue and seashell pink products, telling me that less was always more. Catholic school teachers scowled and threatened repercussions at the slightest hint of "provocative" makeup. And even when I saw humans with pale skin pull off striking cosmetics, I told myself those looks weren't for me.

After being inspired by many beauty vloggers’ dark lip routines and an Establishment story about the unselfconscious "toddler grandma” approach to fashion, however, I decided I was finally going to do it anyway. I was going to stick it to the makeup man, be brave, and wear Kate Moss’ velvety-red Kiss Of Life matte lipstick for the first time.

Kate Moss Matte Lipstick, $5, Target

It's largely been exploring my gender identity that has given me access to progressive discourse surrounding why it's so damaging for people to perpetuate the idea that benign things — sports, skirts, makeup, technical jobs — are for some humans, and not for others. Recently, I started to wonder why I could be so adamant about abolishing outdated gender assumptions, yet so tentative when it came to the products or clothing I wanted to wear.

Once this first seed of doubt regarding my previous refusal to rock red lipstick was planted, however, my natural stubbornness finished the job. "I am going to do this and I will look amazing," I thought. "Suck it, makeup counter people."

My thoughts upon putting the lipstick on and looking at myself in the mirror went something like, “Wow, OK! This isn’t as bad as I thought it would be. It’s nice. It’s not on my teeth. And if I put on some eyeliner and mascara, it’ll balance things out just fine."

My thoughts upon taking one step onto our porch? “Oh my god, everything is wrong. This is going to make my teeth look yellow. I definitely just touched it. It’s probably smudged and on my teeth.”

I soldiered on, however, and chose a low-stress place to debut the fresh look. My wife was on the hunt for new glasses, so we were going to a small mom-and-pop store. It would be fine, I figured. I would forget I even had red lipstick on.

This was a lie. You see, when you go to a store that sells glasses, there are usually mirrors. A lot of them. Every time I turned around, I was faced with myself. My lips flashed of ruby-red, and I couldn't ignore them. It was at this point that the politics of my weight came into play.

When you’re a fat human, being stared at is rarely a new experience. But as I grew more and more uncomfortable — certain that everyone in the shop was looking at me — I couldn’t take my usual, “I look great, screw 'em if they don’t like me,” approach.

Sometime around the 10th pair of glasses I tried on, however, I decided that I needed to suck it up.

I took a quick look around the room: A few old dudes were milling around, picking up wire-rims. A couple of middle-aged moms were with their kids, selecting glasses with soccer balls on the earpieces. No one was looking at me at all, even if it felt like they were.

I realized then that it's easy for me to remain positive about other people's identities and bodies. If my mom, who has the same skin tone as me, had asked me whether she would look good in red lipstick, I would've said yes in an instant, and I would have meant it.

But when it comes to myself, wearing dark makeup isn’t just hard because I’m pale and wish my teeth were a little less scarred from three years of braces. It’s hard because dark, bold beauty looks draw people’s attention. And if I have their attention, they'll have a prime opportunity to see all my "flaws." For me, wearing eye-catching makeup has long felt like being onstage in public-speaking class. All eyes on me, and not in the good way.

That feeling is exactly why I’m going to continue wearing it, though. I’m not the kind of person who shies away from new or challenging experiences. So if I think dark makeup can look stunning on other pale, fat humans, I want to work past feeling that it can't be stunning on me.

I wish I could tell you that my one day of wearing dark lipstick boosted my confidence through the stratosphere and made me want to wear it every day. That didn’t happen. But it did make me feel certain that one day I’ll put on dark lipstick and walk out the door like it’s no big deal.

Maybe I didn't feel great while wearing red lipstick out and about, but I did feel proud of myself for deciding to change up my style and for moving outside of my comfort zone. I had nothing to lose by trying something new. Sure, I felt self-conscious — and when I got home, I realized that my lipstick-newbie self had, in fact, gotten lipstick on their teeth — but that brief embarrassment wasn't world-changing. What was world-changing was the beginning of a process I hope will end with me being consistently braver while wielding a lipstick tube, mascara applicator, or eyeshadow palette.

Images: Sam Schooler