Growing Up Meant Learning How to Wear Red Lipstick

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Photo: CSA Images/Getty Images

There has, to the best of my memory, never been a time when my mother has left the house without lipstick. When I was young, she would not consider taking the garbage to the end of our driveway without applying a quick coat, strange though it may have looked in combination with the housecoat and slippers she was wearing. I can recall her putting it on before making an important phone call, or quickly painting it on should someone she deemed important be on the end of the line when she answered. Even now, with her health and mind failing and so many daily routines lost to the circumscription of illness and confusion, there remains the lipstick.

My mother is not vain. On the contrary. She was and is fully a product of her generation, which came of age at the height of the socially strict 1950s. Lipstick to her was public evidence she was adhering to expectations placed on her as a young woman, ones she’s never been fully able to shake. The absence of it — much like the absence of a slip, or a mismatched color, or a dropped hem — was to invite shame from the silent, judging masses of the outside world.

It was through this restrictive prism that I viewed makeup for much of my adolescence: as some sort of proof I was doing what I was told, following rules that, though I could not have articulated it at the time, seemed very invested in my sitting still and being made acceptable to people I had never met but whose opinions inexplicably mattered. And so, barring one explosive collision with blue eye shadow (the result of a Mary Kay makeover I received on my 13th birthday; this was the late ’80s, after all) and despite my mother’s gentle but relentless prodding — “Why don’t you try a touch of color on your lips? It would really make that outfit/that hairstyle/your eyes pop” — I remained mostly makeup-free until well into my 20s.

Then I moved to New York City.

From the moment I emerged from the subway, it became very apparent that if I intended to stay and not be dismissed as a tourist immediately, or worse, someone unable to shake her deeply suburban upbringing, I needed to up my look game. Or, rather, have a look game. These women streaming past me on the sidewalk with their bold faces — outfits can be tougher to assess on a crowded New York sidewalk, especially in the cold months, but no one misses a standout face — so put together, so silently declarative, clearly knew who they were and what they wanted. These were not women seeking approval or attempting to blend in. These women were fearless. 

No one embodied this look more fully at the time than Carolyn Bessette-Kennedy. She had married John F. Kennedy Jr. the year before, and her strange, compelling face, white, buttery chunk highlights, minimalist style, and red lips were still mesmerizing to the ruling media and fashion powers; the papers were plastered with photos of her suburban-cum-sophisticate overhaul. She never spoke publicly, and something about the blank slate that silence offered made the commanding image of Über–New York chic she presented seem more accessible, as if her metamorphosis were replicable. Thanks to the restraints of budget and Mother Nature, I could never hope to truly emulate her style (nor did I ever yearn for her actual lifestyle), but the lips? The lips were in reach. It seemed to me if I could get those lips, the rest of the mysteries of life in NYC would unfold for me. Before my second week was over, I’d worked up my nerve, walked up to the MAC counter at Saks Fifth Avenue, and purchased my first tube of Russian Red.

The first time I wore it out, to a Soho club, I suffered from an irrational fear that the lipstick police would appear and ask me to remove it, as though I hadn’t yet earned the right to be so bold with my own face. This was not my mother’s lipstick. My mother hewed to browns and peaches, colors that not only did not suit me but felt like the lipstick equivalent of a slip or sensible heels. This was … well, they don’t call it fire-engine red for nothing. It was impossible to miss. All I had to learn now was how to be someone who didn’t want to be missed.

That my mother and I have such conflicting views on lipstick seems entirely in keeping with its fraught history. Like nearly everything having to do with a woman’s appearance, red lips have been both loved and loathed for centuries. Cleopatra reportedly mixed together crushed ants and carmine to color hers. Queen Elizabeth would paint her face white and her lips red as a show of power, and to ward off evil spirits; 200 years later, the British Parliament outlawed makeup entirely, claiming it was the stuff of witches (read: prostitutes) hoping to ensnare men. At the same time in France, makeup was a sign of royalty, and prostitutes were bare-faced. Since the mid-20th century, red lipstick has been the mark of Hollywood, glamour, desire, perfection, and sex.

Of course, the real trick with red lipstick is to keep it from wearing you. This has less to do with application than, as with almost everything done well in life, how well one knows oneself. There is a great scene in Lena Dunham’s Tiny Furniture when Aura (Dunham) turns up for what she thinks is a date with Jed (Alex Karpovsky) wearing a too-red, too-heavy, very out-of-place lipstick only to discover he is not terribly interested in her and just wants a place to crash. The desperation and thrust for self — the aggressive attempt to project a person you aren’t yet but very much want to be — so perfectly captured in those misplaced lips succinctly sums up most of my 20s, when I hung on to that tube of Russian Red as both a promise of things to come and proof I was headed in the right direction.

For a long time, it was the only lipstick I owned. Even after my career began to take off and my social life (and wardrobe) began to more appropriately dovetail with my makeup choices, I stuck with it. I carried it with me at all times: proof that I was prepared for my day to take me anywhere, a familiar assurance, something strong and reliable I could lean on.

Then, one evening in my early 30s, after an especially long day at work, I walked into Bloomingdale's on a whim. It was payday, and I wanted to reward myself for surviving. I wanted to feel like someone new. After some wandering around, I picked up a Chanel Gabrielle because, well, it was Chanel, classic and chic, two things I felt very far away from at that moment. Fairly quickly, the Russian Red dropped to the bottom of my makeup bag. Not that long after, my co-workers went to a promo event for Tom Ford’s inaugural lipstick line and returned with a tube of True Coral for me (or what I like to refer to as “old-lady Miami beach”; one needs both heat and a sense of humor to pull it off). It reminded me of women from the ’60s who applied makeup as though it were war paint. A few weeks later, I snagged an explosive Dior 999. A few months after that, I forgot my makeup bag on the way to a dinner and ran full-tilt into YSL 001, the lipstick equivalent of a full-length mink boa. It is not for the faint of heart.

At last count, I owned 16 lip colors, all of which to the naked eye likely appear within one degree of each other but, to me, represent a sliding scale of strength. Some days I apply as evidence of how great I’m feeling; other days I lean on red lipstick to make up for what I lack. That nonnegotiable mark of color has become a small daily reward to myself, a final perfect piece in the daily puzzle of putting myself together to meet the faces that we meet, an armor against the world. Here I am, I say to myself, red X marks the spot. But also: Stand back. Make way.

I recently returned to my Russian Red. It feels reliable and tame now, like a well-cut blazer. I have, to date, never applied any of my lipsticks to take out the garbage. When I want to pass quietly by, unremarked on, I wear no lipstick at all. But much like my mother, I would never, ever consider going anywhere without it. I imagine myself in the future, aged and wrinkled, possibly lying on a beach in Miami, a slash of red on my lips the last evidence of a life fully lived. The other day, on our way out the door to move her to the nursing home where she’ll be living from now on, the last thing she asked me for was lipstick. I handed her mine. “What a lovely color,” she said, quickly applying it before we walked out to the waiting car.