A couple of months before my novel Startup came out in April 2017, I got drinks with my friend Amanda from work. Amanda is 10 years younger than me and an incredibly smart reporter. “So,” she said, as we sipped our drinks, “how do you feel about your book coming out?”

“I feel okay,” I said. “I mean, I feel good. I just don’t know what to expect.”

“It will be great,” Amanda said.

“I hope so,” I said. “I just want to be able to call myself a novelist. Does that make sense? Like, when do I get to call myself ‘a novelist’?”

Amanda looked confused. “Um, right now? You are a novelist! You wrote a novel!”

She was right, of course, but it was hard for me to wrap my head around. Even though my book was being published by a major publisher, even though it had already gotten positive early reviews, I still felt like an interloper in the fiction world. Who was I to think that I could just swoop in and write a novel? But no, I had to remind myself, I had worked really hard on the book. And my book was good. I could call myself a novelist.

It struck me that I was still struggling, at nearly 40 years old, with the same issues I’d had for so long: Where did I belong in the world, and what contributions was I going to make to it?

Turning 40 was a real maelstrom of mixed emotions. Hanging over everything was the fact that I still wasn’t pregnant. And even though my book launch had been a success, I was still struggling with questions of identity. Not being pregnant made me feel broken, like I sucked at doing this really basic thing that literally billions of people have done for centuries.

And my internal struggles were spilling out into how I presented myself to the world. It turned out I had no idea how to dress myself anymore. For most of my thirties, I’d had a work uniform: floral or patterned silk top, skinny jeans, ankle boots. Sometimes I’d invert it and do patterned pants with a solid color top; there had been some slight variation with button down plaid shirts and skinny jeans when I was at Rolling Stone because I was, consciously or not, trying to fit in with the guys who worked there. But now, when I put on skinny jeans and a top, it didn’t feel like me anymore. The jeans weren’t especially comfortable, and in the morning I scanned my closet in increasing desperation as I eliminated each shirt, one after the other, from daily contention.

I was also having trouble shopping, which had historically been a pastime that I truly enjoyed, perhaps a little too much. But now, when I went into my old standby stores—shops like Madewell and Topshop and Club Monaco and Zara and H&M—I was having an increasingly hard time finding clothes that appealed to me, and actually fit. My turning 40 also coincided with the truly unfortunate fashion trend of one shoulder or shoulder-cutout tops, a look that was very difficult to pull off without a strapless bra, and I’m sorry, but if you’re above a D cup, there is no strapless bra on the planet that will be comfortable for you. (If there is, please send one to me.) I could have worn one of these shirts or dresses with my sensible beige Maidenform racerback bra showing, but that seemed to negate the whole point of these tops in the first place. Not wearing a bra wasn’t an option; it’s a matter of physical comfort. It’s achy to have them just flopping out there in the wind (and don’t even get me started on boob sweat).

I had never been someone who felt like I needed to “dress my age,” and yet now, all of a sudden, I was willing to dress my age but I had no idea what that even looked like. What were 40-year-old women even supposed to look like?

I have, for better and (for my own mental health) for worse, always been someone who cares about how I look, and how other people think I look (see also: Revenge Jacket Doree). And I have also always been a faithful student of the people around me and what they were wearing, like a little proto-Harriet, always watching and absorbing.

Joanna Degeneres

When I was four, a girl in my class at daycare had a pair of yellow clogs that I wanted so badly. I begged my mother for them and she (wisely) said no, that I was only four and I would probably break my ankle. So I didn’t get the clogs, but I did get extremely concerned with having cool clothes and shoes. This really picked up speed in third or fourth grade, when I finally persuaded my mom to buy me a Benetton rugby shirt, which seemed to be the absolute pinnacle of cool at the time. Don’t forget, it was the eighties, and some diabolical genius had convinced us all that rugby shirts with huge logos on them looked amazing. “It’s literally just a shirt with a big brand name on it,” my mom said, and I nodded enthusiastically. Wasn’t that the whole point, to show everyone you could be part of the club by wearing a really dumb-looking shirt with a truly massive logo on it?

By seventh grade, I could buy my own clothes because I had my own money thanks to babysitting, because at the time, 11 or 12 was a perfectly reasonable age to watch other people’s children for money. This meant I had enough money to go to the juniors department at Filene’s in the Chestnut Hill Mall in Chestnut Hill, MA, aka the fancy mall that had a Laura Ashley store and a Houlihan’s, and buy, for $60, a pair of tight, acid-washed Guess jeans with the triangle Guess logo on one of the back pockets. This seemed like the most money that anyone had ever paid for a pair of jeans, and I counted out the cash slowly and proudly and wore those jeans with my Nike Airs and my teased bangs until, all of a sudden, it was the nineties and “tight” and “acid-washed” and “teased bangs” and “pegging your jeans” were no longer part of the teenage fashion lexicon. Instead it was all about going to the Urban Outfitters on Newbury Street or Harvard Square and wearing flannels and Doc Martens and vintage overalls and “streetwear” brands like Stüssy and Fresh Jive. Probably because I lived in Massachusetts, I’d had an intermediate stop in preppy land—J.Crew rollneck sweaters, moccasins from L.L.Bean, a CB jacket with ski lift tags hanging on the zipper all winter, you get the idea, it was all sort of tragic—in between the phases of looking like I’d walked off the set of a John Hughes movie and onto the set of a Nirvana music video.

Being a teenager sometimes feels like you’re the costume designer for the movie of your own life (but of course, actual movies like Clueless and Kids, which both came out the summer after I graduated from high school, were hugely influential too). Every time I decided to start dressing a different way, it required an almost entirely new wardrobe, although there was occasionally some overlap: For example, I’d procured a few flannels when I was in my preppy phase, which transitioned seamlessly into grunge.

But one of my biggest fashion influences during that time was my friend Beth, whom I’d met the summer after my senior year of high school when we both worked at a restaurant on Newbury Street in Boston. Beth was a year older than me, a photographer and film student at NYU, and she was cool. She was living for the summer in an apartment in Cambridge with her older brother—again, cool, seeing as I was stuck at home— and as soon as we got off work, we’d traipse down Newbury Street, sitting on the floor of Tower Records and reading magazines for hours, sipping coffee at Espresso Royale, trying on clothes and shoes at Allston Beat. She wore drain chains for necklaces and babydoll tees and baggy pants, but also slips as dresses and turquoise nail polish. One night, I met her at her brother’s apartment, and we went out in Harvard Square. I had carefully considered my outfit for our excursion, which deliberately channeled Garbage front woman Shirley Manson, if she had shopped in the bargain bin at Urban Outfitters: a zebra-print velour mini skirt, a short-sleeve black polyester collared shirt that looked vintage but wasn’t, fishnets, black John Fluevog boots, and a red patent-leather spiked bracelet.

It was a Look. Of course, “looks” are different when you’re 18 and using them as armor, to try on an identity you’re not quite ready for. But now I was 40, and I was, once again, tentatively dipping a toe into a new identity, except this time it was wearing a sensible low-heel shoe with a nice wide toe box. I had naïvely thought that, as I aged, I’d be able to continue operating in the same way that I had been since I was a teenager: There constantly would be a plethora of trends and looks for me to choose from, and all I had to do was select one. And while on the one hand I resented the idea that I should “dress my age,” I also really just wanted to … dress my age. I didn’t want to wear anything tight or see-through or too short; I wanted to feel comfortable, but not like I had totally abandoned all pretense of caring about how I looked, because I do care about how I look and I don’t want to pretend that I don’t. But all around me, all I saw were clothes that I couldn’t imagine putting on my body.

“Is this where I admit that I now understand the appeal of a store like Chico’s?” I asked Kate. “Like, all I want to do is dress like a funky art teacher. I never wanted to look like this before.”

“Yes. I get it. I now understand the appeal of purely comfortable clothes,” she said.

“What is happening to us?” I said, laughing. “I guess I just never thought this would happen to me.”

Then, one day, I was in a shop near my house and I spotted a sleeveless, oversized, black linen jumpsuit. I tried it on. It was looser than almost anything else I owned, but instead of feeling like a blob, I felt airy and free. It exposed my upper arms, which I had historically kept covered because … why? I suddenly wasn’t sure. I thought about how all my body insecurities—my “flabby” upper arms, my “paunchy” stomach, my “too thin” legs, my “too thick” waist, my “flat” butt, my “big” boobs—had dictated what I wore and, perhaps more significantly, what I didn’t wear. It seemed exhausting, this automatic fixation on “flattering” clothes and covering parts of my body up that didn’t need to be.

I bought it. It became my nonwork go-to, the item of clothing I wore most often. It felt both slightly childish and, somehow, with its lovely drape, sophisticated. I felt more like myself than I had in ages.

From the book: Thanks for Waiting: The Joy (& Weirdness) of Being a Late Bloomer by Doree Shafrir. Copyright © 2021 by Doree Shafrir. Published by Ballantine Books, an imprint of Random House, a division of Penguin Random House LLC.