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Billie Eilish is my fashion icon. I’m a middle-aged mom.

Here’s how a teenage music phenom inspired me to stop stressing about dressing

Perspective by
November 14, 2019 at 10:45 a.m. EST

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This shouldn’t be so hard. I just need to put clothes on my body so I can leave the house. So why am I standing paralyzed in my closet with a pair of boots in one hand and leopard-print flats in the other, feeling tears welling behind my eyelashes?

As a middle-aged suburban mom who works from home, I find getting dressed both a conundrum and an emotional minefield. There is no longer an easy prescription to follow when I’m choosing what to wear.

When I got my first real office job in the late ’90s, there was an actual employee handbook, complete with a list of forbidden wardrobe choices:

I wore low-heeled pumps and had a dressy raincoat for work. When I was a stay-at-home mom with a baby spitting up on my shoulders or a toddler to crawl after, I gave almost no thought to what to wear — what’s clean, what won’t be destroyed, what can I move in? And later, when I taught middle school, I chose my outfits to split the difference between professional and quirky: put-together enough to impress my principal, but strange enough to hold my students’ interest.

But now I work from home and it’s just me. Morning after morning, I stand in my bedroom picking up one item after another and wondering, who am I? Who is the woman who wears this sweater? What do these silver hoop earrings declare to the world about my level of intellectualism? Is there any universe in which these Smartwool socks could be considered sexy?

Clothing is one of our most basic markers of identity, after all. Look at that iconic image from movie posters for “The Breakfast Club.”

How do we know which one’s the jock, which one’s the outcast? It’s all about the fashion choices. I learned this in middle school just like everyone else.

But this conflation of style with identity seems to be the root cause of my anxiety. If I could pick out the right shirt, it would tell the world who I am. My haircut, my shoes, my earrings, my makeup, the exact fade and cut of my jeans ... It would all coalesce into a definitive statement about my precise blend of intellect and whimsy, wholesomeness and grit. But that means I have to know exactly what that is.

At this point in my life, I have read countless articles in women’s magazines urging women over 40 to dress their age. Apparently, we are supposed to stop chasing trends, stop dressing too edgy or too sexy, and start accumulating a wardrobe of “classic” pieces. We’re supposed to settle into a certain seriousness when it comes to the way we present ourselves to the world.

Except that doesn’t sound like any fun.

Instead, I have decided to take my style inspiration from the 17-year-old musical phenom Billie Eilish. No, this doesn’t mean that I’ve dyed my roots green or started wearing extra-large sweatshirts and stacks of silver weaponry disguised as jewelry. Eilish is impossible to copy, and even trying to ape her unique aesthetic would be a poor tribute to what she’s taught me.

What I’ve learned from Eilish isn’t her particular blend of goth/hip-hop style, or even her courage in defying stereotypes and challenging notions of femininity in celebrity culture. Rather, the message I’ve adopted and applied to my own fashion choices comes straight from her music. Eilish doesn’t adhere to the traditional singer-songwriter model — her songs aren’t the story of her life. She’s no poet of the confessional school. She writes her songs in character, telling stories from a wide range of perspectives that she puts on and takes off like costumes: serial killer, seductress, devil, unrequited lover, the monster under your bed. As a result, her songs cover a terrain as vast, varied and strange as human experience itself.

The curious thing is that this approach results in viscerally honest, emotionally wrenching music. It can be ecstatic, or tender, or filled with bravado, or whispering with fear. It can be all of those things at once. And her fans, like me, can relate. Because somewhere inside of us, there is a tiny piece of the serial killer, the seductress, the devil, the unrequited lover, the monster under the bed. We can be all of those things.

So maybe, as a middle-aged mom in the midst of career uncertainty and changing family dynamics, I don’t have to know who I am. Maybe there doesn’t have to be only one answer. And maybe I don’t need to find a single fashion aesthetic to express my identity.

Some days, I’m tired and I just pull on jeans and a T-shirt, dressing the part of a work-from-home mom. Other days, I go to the grocery store in combat boots and a floral duster. Or pick up the kids from school in a jumpsuit and platform sandals. Or curl my hair and put on red lipstick and a vintage dress to sit down at my desk and write.

After all, I’m over 40. I’ve been a lot of different people: the teenage rebel in the motorcycle jacket, the office worker in the pantyhose and silk blouse, the middle-school teacher in the comfortable shoes. I’m a mom and a writer and a wife and a gardener and a music fan and a great cook and a friend and a rotten housekeeper. I go to malls and indie record shops and the veterinarian’s office and charity galas. I love playing guitar and long walks and dog kisses and teenagers and complicated recipes and taking pictures of moss. I contradict myself, I contain multitudes, etc.

So why not dress the part?