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On a muggy summer day, two women rang my doorbell, came inside, and began bagging up most of my clothing. They folded up things I once loved—a fit-and-flare polka-dot chiffon dress; a funky vintage silk shirt—and stacked them neatly in garbage bags to be donated or tossed. It could have been horrifying, except that I'd invited them to do it. Having recently turned 36, I'd decided to act on an increasingly nagging feeling: Few of my clothes really seemed like "me" anymore. I felt more adult than ever—hitting your midthirties is one of those markers you can't ignore—and yet I still wasn't quite giving myself permission to buy what I really needed, was still haphazardly splurging on whatever caught my eye, still holding on to low-rise jeans and glittery dresses and outdated boots I never wore. I wanted a new start, an opportunity to redefine myself. But I found it hard to let go. Some clothes I associated with my mother, who had recently died, or with the year I wrote my first book or met my husband. My clothes weren't just practical; they held my memories. The history of my life, written in silk and cotton and rayon.

A woman in her late thirties or early forties is not old, but not young, either. In your twenties, the world handles you, alters you, but it also leaves you— thankfully—surer of yourself and more amused by your flaws than you once were. After my mother died, I knew myself in ways I hadn't before. I also had quit my office job to write full-time at home in Brooklyn, along with teaching in an MFA program. As a professional with hard-won achievements behind me, I wanted my clothes to reflect a person touched by life, someone who knew a thing or two about what she did and did not want.

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Figuring out how your wardrobe might reflect your changing persona is not just a doctrinaire matter of ditching the miniskirts and youthful polka dots. It involves figuring out your own visual language, which isn't easy. My friends kept telling me that they, too, were facing this dilemma: They wanted their wardrobes to reflect new identities—as mothers, bosses—but weren't sure how to achieve that. We all were having difficulty saying goodbye to our former selves, even as we all sought a new style, one that would feel like us. I knew I'd gone from liking a girlish, "pretty" look to one that was polished, tailored, pulled together, if still playful. Beyond that, though, what would that look be? How do you build a wardrobe that's grown-up but not severe?

One of my earliest memories: It's 1982, I'm six, and my mother is dressing for dinner. She transforms as I watch. One minute she is my regular mother, the one who cooks me dinner in jeans and a sweater; the next she is a beauty in high leather boots and a faux-leopard coat, dabbing Shalimar behind her ears. Like that perfume bottle, her closet is a kind of magic that, once opened, can change everything. At 29, she could be mistaken for Ali MacGraw in Love Story. She has a taste for the theatrical and makes some of her own clothes, including a floor-length burgundy velvet dress, its plunging neckline delicately trimmed in white. I put on the velvet dress and step into her rich leather boots. None of it fits—I look ridiculous—but the dress drapes around me like the promise of a future self, indistinct but glamorous, the way that my mother is glamorous to me.

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For years, I sought that touch of theatricality, that subtle drama. In my teens and early twenties, I scoured Goodwill and East Village thrift stores for a look that expressed the paradoxes of my personality: I was fundamentally polite, eager to please—a typical eldest daughter—but as a young poet, I had an unconventional, creative side. I gravitated toward vintage with a touch of the eccentric. I remember a bright blue Himalayan wool coat with a peaked hood, white embroidery, and adorable pompoms; purple Levi's cords worn with a 1970s-style green suede jacket.

By my midtwenties, I'd added more classic and "officey" things, but I was always a little broke, loath to spend too much on any one item. The result was haphazard: half of my closet cheap fast fashion that pilled or frayed, half of it idiosyncratic high-end pieces bought on sale. Instead of investing in well-cut black trousers, for instance, I'd go to a sample sale and buy a floor-length Catherine Malandrino dress embroidered with birds. Or a chic Miu Miu gingham-skirted shirt-dress—80 percent off!—which, lovely as it was, never got out much.

Flash forward: I'm 33, dressing for an event I'm hosting. I look at my closet: The draped dresses with short skirts seem young; the wry Anthropologie pieces with their 1940s tailoring and floaty princess sleeves, too soft; the low-rise jeans, not only dated but just wrong.

For a time I update by buying a piece here, a piece there, but nothing that coheres. Then one day my oldest friend tells me she has hired two women to revamp her wardrobe. When we meet for drinks, she looks more grown-up, more seamlessly put together—a woman who has made the shift from girl to adult.

And so, on that August day, I waited at home a little nervously to meet Mauri Weakley and Carly Beck, my thirty-sixth-birthday present to myself. They had worked together at Steven Alan, the mecca of low-key Brooklynite chic, where Beck was brand director and Weakley was head merchandiser. Now Weakley co-owns a local home-goods store, Collyer's Mansion, Beck has a handbag line, C.A.B, and they "cleanse" on the side. By the time they arrived, I'd gotten rid of two bags of clothes. I proudly told them I wasn't sure we'd need to get rid of much more. I was wrong.

The "closet cleanse" has become such a staple of reality TV that we all know what the process looks like. (Keep! Donate! Mend!) But what often goes unexplored in these episodes are the deeper feelings we invest in our clothes—fabric and cut as forms of memory; how a skirt can speak to our private ideas of self.

I had thought a lot about these deeper meanings, but I had no idea how to act on my desire to shed the past. Now, as they went through my closet, laying out everything I owned with gentle but pointed commentary—this dress was "too 2004"; as for those old stained boots, "Did you work on a farm?"—I found I was actually enjoying myself.

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Turns out letting go of so much at once is invigorating. It gives you permission to be the person you really are now. With their help, I found it surprisingly easy to part with not just my quirkier pieces but also the spontaneous twentysomething self who'd bought them. It was almost a relief to see her disappear, like a relationship I'd outgrown. (Though I did let myself keep one or two pieces in a box for sentimental reasons.) By the time we'd discarded more than half of my closet, I was feeling buoyant; thoroughly delighted to be "breaking up" with my old self. It was like being absolved: Gone were the visual reminders of past impracticalities, failed shopping experiments. What remained in my closet was the me of today, more casual, hopefully a tiny bit wiser—plus so much extra space, where the future beckoned.

Now it was easy to see what I needed for my new life: two or three good skirts (not 10), lots of grown-up denim, some flats, belts, more of the boxy tops that flatter my long torso, and easy-to-wear dresses. Beck and Weakley suggested I buy a batch of black and white T-shirts and tanks and two pairs of black boots— one low heeled, one higher. They also suggested Rag & Bone jeans in dark colors to go with my remaining shirts; half a dozen lush, textured sweaters; a beautiful beaded black belt, which was both basic and a little theatrical; and a black-and-white skirt that's easy to pair with nearly anything. (The old me would have bought something much more "original"—in canary yellow!—only to realize I had nothing to wear it with.)

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Ultimately I spent more money at one time than I ever had before, which made me vaguely sick to my stomach. But—for once—I use everything I bought. And the process reinforced my own new impulses: to buy less stuff, but of a higher quality; to shop less often, but in larger batches; and to be sure that each purchase plays a necessary role. My "unique" pieces have been streamlined, and my new gurus helped me see that playfulness can be achieved instead through rich color or detail. (Of course, like everyone trying to develop a new habit, a few months later I still find myself making the same old mistakes on occasion, deluding myself that, say, that alluring floor-length gown is just what I need.)

What does it actually mean to "dress your age"? There really are no rules. I have a poet friend who's almost 50 and still dresses like a girlish 20-year-old— but it suits her, because what she's really doing is dressing her self. Clothes are like totems: visual extensions of ideas we have about who we are and what we're capable of. Which is why it can be so hard to let go of them. They contain pieces of selves we were and selves we wanted to be but never will be—a realization that intensifies as the years pass.

Achieving that "youthfully adult" look is genuinely hard (and probably beyond my capabilities without professional help). Maybe that's why so many women are attracted to the idea of a uniform. These days, I'm drawn to what the writer Janet Malcolm called "the interestingly plain," but with a bit of surprising detail—serious but not sober. I have less "stuff" but more options. Better yet, I feel like myself again. I imagine that someday I'll want to do it all over. I won't hesitate next time.

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