I’m standing in front of a wall of Make Up For Ever lipsticks at Sephora with not one, but three resident “Color Experts” at my side. It’s a Friday evening and the store is booming like New York’s hottest club (Stefon, back me up on this). I reach for a nearly-black Azealia-Banks-“1991”-esque tube but am practically hand-slapped by the Color Expert with a heart drawn next to her eye. “If you’re a fashionista and like to keep up with the trends,” she says (BTW: how could she read me so easily?!), “then you’ll want to go for lighter, brighter colors for spring and summer.” I’m also instructed to limit my testing to three lipsticks—any more than that, they tell me, will cause the skin around my mouth to become red and blotchy, rendering any color disagreeable. I nab a creamy pink, a classic red, and am handed their seasonal pick: a very J.Crew peach. The pixiest of the three Experts leads me to a chair to try them on.
But let’s back up. A few days earlier at the Gloffice, as a rare tube of RiRi Woo was being passed around, discussion turned to the Bold Red Lip. “I just started wearing red lipstick last year,” I confessed. Emily picked her jaw up from off of the floor. “I have a really small mouth,” I said. Emily and Nick clearly weren’t following. “Why does that matter?” asked the amply-lipped Weiss. Well, doesn’t it?
While I’m currently very comfortable, nay, downright confident, wearing any and all shades of lipstick, I wasn’t always this way. I grew up in the Bay Area, but I’m originally from Upstate New York, where a Bold Red Lip looks just as out of place as a Kardashian at a Phish show. And even in California, I ran into trouble: on my first day of high school, our resident Regina George introduced herself to me by cooing, “Aw, you don’t wear makeup—that’s so cute.” Kill me.
Apart from feeling over-dressed—and uncomfortable—in bright lipstick, it was also around this super-pleasant adolescent time of my life that my then-boyfriend started to tease me about the size of my lips. (In his defense, my mouth is actually so small that I don’t even have a full set of adult teeth; some had to be pulled—my dentist is a fantastic editor.) But, still, leave it to a boy to wreak havoc on your self-image.
I distinctly remember this one line from a Russian novel I read for a class: “All women are lips, nothing but lips.” Did that mean I was destined to be a sub-par woman? And if so, I certainly wasn’t going to elaborately decorate my female flaw. So when I wasn’t sneaking coats of Lip Venom and/or Lip Injection in the bathroom to amplify my “puny, lifeless” pout—Too-Faced’s words, not mine—I did my best to draw the focus to my eyes and cheeks. I thought of that saying about playing up your best features or whatever, and clearly my mouth was not among them.
But by the time college rolled around, I was ready to redefine myself in New York City. In fact, I bought my first tube of lipstick—a baby pink by Maybelline—at Duane Reade on the night of my first Misshapes party. (It was meant to round out this Valley of the Dolls moment I was trying to have, OK?) I was in love. Though nearly sheer and imperceptible, the act of applying it made me feel so… feminine. Later that evening at Don Hill’s, my chunky white headband, teased hair, babydoll dress, painted lips, and I all had a fantastic time trying our best not to smile. And when I (we) felt bored or fidgety, suddenly there was something to do: reapply!
I stuck with my trusty Maybelline for a few years after graduating, until I just felt ready to big up my lips. I wish I could recall the exact catalyst. Maybe it was the change of environment—you know, becoming a Working Girl—or being (and feeling) older, or the fact that my face was finally growing into its features (or vice versa…) or just not caring about what other people thought anymore, but it happened.
Gwyneth Paltrow is widely quoted as having uttered something to the effect of: “Beauty is about being comfortable in your own skin. That, or a kick-ass red lipstick.” I wanted all of that. I went out and bought tubes of Nars red, orange, peach, and pink, and a dark, dark purple from MAC. And I still wear them everywhere, no matter the time of day or year. (I’ve also made a point to avoid boys who make you feel bad about yourself, which gets easier with age.) And while I can’t imbue all diminutively-mouthed women with my late-onset confidence, I can leave you with my Sephora Color Expert’s words of wisdom:
- Everyone hates themselves in lipstick at first: “It’s just shocking.”
- Using a brush will give you more control, not only in the precision of the line but in the amount of product you’re putting on.
- Applying too much lipstick will cause it to bleed faster. If you apply the right amount, you should only need to retouch after eating (or not even then, if you’re Jen Brill).
- Resist the urge to turn up the volume on the rest of your makeup to match your bright lip.
In conclusion: I now think of lipstick the way I think of karaoke, which is to say I’m somewhat cautious of it, but I realize it’s much less about a god-given gift than it is about committing to it and feeling confident. Sometimes we can’t be tied down to what’s “recommended” for us: big or small lips, pear or apple shapes, large or small busts. And I, for one, no longer care to be advised that dark colors will make my lips look smaller. Do you see Lily Cole, KStew, or Jennifer Aniston backing down? No. Rules are meant to be broken.
Mackenzie Wagoner—the newest member of Team ITG!—photographed by Emily Weiss in New York on May 13, 2013. [2,3] Photos by Mackenzie Wagoner,  Jennifer Aniston,  Kristen Stewart,  Lily Cole