Lipstick loud: Why I’m embracing a bold lip in midlife

Cruella was my gateway: An orange-red shade of the NARS Velvet Matte Lip Pencil. I’d purchased her six years ago, along with a more neutral, pinkish brown I picked up at the same time. I had never been big on lipstick — it felt incompatible with my low-maintenance vibe — but what can I say; I was feeling curious. (Also, I was on vacation in NYC.)

Back home, the neutral shade became my go-to, and stayed so into my late 40s, while Cruella — that bossy bitch, that loud talker — stayed tucked away in my makeup drawer. She waited, patiently. And then, on a spring evening about a year ago, right after I turned 50, I had a big work event on tap — my arts nonprofit’s annual fundraiser — and I brought Cruella with me. That night, everything changed. 

In midlife, I have become a woman who rocks a bold red lip. It came on like a crush — a new fascination, a new plaything, a new tool in the evolving self-image kit. I was determined to bust into my fifth decade on this burning planet with joy and defiance, so perhaps it’s no surprise that, basically overnight, I became a lipstick lady in the loudest way possible. Cruella has friends now, a regular harem of reds. There are no fewer than six different tubes in my bag, and while I still consider myself a lipstick rookie, I could wax poetic about the pros and cons of each. 

Over-50 makeup: The pleasures and perils of painting one’s mouth 

Like most obsessions, this one isn’t without awkward moments. I have ended up with red lipstick on the wrong parts of my face, on my teeth, my fingers. I leave a trail of crescent-marked coffee cups — a thing old me once found repugnant, when the lip traces weren’t mine — and have sat through meals full of lowkey worry that I’ve unintentionally achieved a bouche mordue that appears more bed-rotting-slovenly than bedhead-sexy. It’s all rather potentially…revealing. 

The anxiety is real: In a piece for Women’s Health, the writer Lizzy Goodman reflects that “a bold red lip was an announcement to all that you cared. That you were trying. That you wanted to be looked at and paid attention to. … it meant saying out loud that I liked myself. Or at least that I liked some parts of my face.” And writing in Self about wearing a red lip for a week straight, Talia Abbas nods to the “overwhelming sensation of feeling like a fraud and being afraid of being called out for it.”

To all of this, I relate. Even if I have the look on lock (there’s no shortage of tutorials, no limit to lipstick-adjacent product), the choice to wear a bold lip in middle age, after years of demure tones or nothing at all, runs the risk of embarrassment, what maybe looks like a flagrant grasping toward vibrancy in the face of received narratives that urge midlife women to go softly into elastic-waist pants, muted shades, and comfortable shoes. (Mind you, I’m personally down with all of the above, and I truly don’t care who does or doesn’t affirm my choices.) 

But a bold lip ultimately feels right for me now; and it feels worth it. It seems of a piece with my relationship to my body at fifty. Lately, acceptance feels like a full-time job: working to accept the natural changes that come with a midlife body, midlife job sitch, midlife me. With age comes constant negotiation with the self, and constant evaluation of what no longer serves us. (There’s no better mantra here than You Do You, but that doesn’t mean it’s a cinch to figure out.) Moi, I have at 50 bid adieu to bikinis and dresses above the knee, but in their place, voila, a bold lip feels like a more-than-fair trade. In spite of the tiny lines forming around my mouth (frankly, one of my most obvious signs of age), and in spite of the popular notion of the “invisible” middle-aged woman — and the demure, over-50 makeup she should wear — I’m throwing down the gauntlet. I choose to be seen, a move I believe will help power me through this evolutionary stretch. 

And there it is, the gift of age: The fucks you left on the side of the road, or in the waste bin at the beauty counter as your received your beautiful new shade of red. I’m demanding attention — in a socially sanctioned, beauty-norms-unchallenged way, sure — but still. And reader, I have to report that, after a year of going about in a bold lip, I feel like strangers are nicer to me. They seem genuinely more interested, more communicative in my presence. 

It helps to have bold friends

I cherish all older, red-lip icons, including some close pals. Take Lisa, who’s 68, and whom I’m pretty sure I’ve never seen without a fresh coat. She wears it to accentuate what she feels is her best feature. “I sit down in front of my mirror, look at my reflection and think, hmm, who do I want to be today?” she tells me. “Do I want to sail out the door, ready to turn heads? To have people offer to carry my groceries? To feel valued as a sexual creature, something this woman still wants? Why yes, I do. I am excited as I think about what to do, how to accessorize, how to make myself into another part of me, a brighter part of me. Which of my many facets will shine today?”

Another one of my bold-lip influencers, my friend Abby, a songwriter and musician in her early 40s, says, “I love red lipstick because it’s equal parts punk rock and classic fashion. It makes me feel both animalistic and refined, both Siouxsie and Coco.” When I ask her if she thinks she’ll keep wearing it after 45, she says, “Forever.” 

And then there’s the Taylor effect. I’d be lying if I claimed Taylor Swift isn’t a catalyst for my new life in red. I kind of like knowing I’m not alone; rather, multitudes of women of all ages are feeling emboldened to rock a red lip for the first time, thanks to the Tay’s ubiquitous mug. It may be a trend, but it’s a trend that’s come along at the perfect moment for me. 

At the same time, Instagram loves to show me another Swift — Rose-Marie Swift, a gorgeous, charming babe in her late 60s, who is also a makeup artist and the founder of RMS Beauty. She rocks a color she calls Ruby Moon (it’s named after her dog, because of course it is), and I can’t look away, I’m smitten. 

Living in the moment, in full color

I think of a favorite photo of me, taken last spring, at the very start of this whole red-lipstick thing—taken, appropriately enough, at the Eras Tour, when my teenage daughter and I snapped a selfie in the bleachers as we waited for the show to start. I love the way I look in it — outrageously happy, my hair up in space buns, mirror-ball earrings, my lips spread wide and red. No, I don’t look costume-y, I don’t look like a woman of a certain age taking a risk with a look that she should have left behind years ago. I look bright and loud in all the right ways; I am holding back nothing, saying everything. 

A year later, I don’t see an end in sight to my bold-lip romance. When I look in the mirror,  I think, Oh, yes. HI!! There you are. I feel pretty. Actually, hot. Like my half-century-old face has awakened with a new pep in its step, as if, in adding this layer of red I’ve uncovered some essential part of myself, a part that the world tries its damndest to bury with its incessant bullshit.

I do wonder if there’ll come a time when I tire of the bold lip look, or the light labor it requires, or my hyper awareness of my own face, and give it up. And then after, when I see pictures from my bold lip era, I’ll smile. With compassion. 

If that happens, so be it. It’s fun, this bold-lip life. It’s a lark, and a bit of a fuck-you, and a pop of color in the drear. For now, I’m all in.