It Took Me 12 Years, But I Finally Got Over My Fear of Lipstick

For day one of lipstick week, I went with what, for me, was a surprising choice: A bold magenta from Pat McGrath's MatteTrance line, appropriately titled "Extravaganza." To be honest, I hadn't intended to jump so quickly into the deep-end of the highly-pigmented pinks. In fact, I'd actually initially planned to start with a more muted beige, and I would have—except that today I couldn't.

Here's the thing: What I hadn’t fully considered before taking on this experiment is that you actually have to consider whether your outfit is going to jive with your lipstick shade, because if not, you risk looking like a vintage Warhol. As a girl who's maintained a pretty grassroots makeup routine all her life, I've never really built a look that way before. But I was running late, and had already decided on a black dress and gold earrings as my OOTD, so magenta lipstick it was!

The minute I put it on, though, I started panicking. Who was this girl staring back at me in the mirror? I certainly didn't recognize her, and I immediately started feeling like a poser. How could a person look so completely different from one measly swipe of lipstick? But I was committed to the cause, so I grabbed my purse and started for the door. "Hey! I like that color lip on you," my roommate yelled after me as I power-walked past her room and down the hallway. Feeling slightly less self-conscious (everyone needs a hype-girl like Diana), I left my building and began my walk to the subway.

But I didn't make it very far.

Feeling as though all of my neighborhood was staring at my newly transformed face, I reached into my bag for my sunglasses and immediately threw them on. I was quickly realizing that it's one thing to wear lipstick, and it's a completely separate thing to own the look. Phase 1 was easy; it was phase 2 that would be the most challenging for me.

By the time I got to the office, I was sweating, and not because the humidity was at an all-time high. I just didn't feel myself, which meant I didn't feel confident. But I pushed through the day anyway, and after a few coworkers told me they liked my lipstick, I began to feel more calm. Maybe I could pull this thing off after all.

I left work that day feeling slightly more emboldened than I had leaving my apartment that morning. I can totally do this, I told myself on the subway ride home. On to the next shade.