When I hit my thirties, dressing went on autopilot: I spent five years working at home in jeans and two more either pregnant or breast feeding. Then I reached 40—and with a lurch realized I had to re-evaluate. What once looked good and felt appropriate no longer seems right. I’m not on autopilot anymore: I’m more ambitious and goal oriented than I was in my twenties, more focused on work than in my thirties. I’m also older—and I don’t want to look as if the elevator broke down at the teen department. Now I want my clothes to communicate that I’m attractive, up to date, professional and competent. I want to look like someone who has achieved a lot—and still has exciting places to go.

But being mindful of my presentation isn’t always easy; getting ready in the morning feels like speaking a new language. Does this outfit make sense? Does it say what I want it to say? On the street recently, I noticed from behind a woman with lovely legs and a black pleated skirt that swung just below her butt. She turned around—and I saw a lined face out of sync with her youthful outfit. She was pretty, but that short, flouncy skirt drew attention to her years in a way that a knee-length pencil skirt, with heels to show off her legs, would not have.

All of this is on my mind as I wend through my closet. I’m not dealing with weekend clothes (I barely have any) or jewelry (is there such a thing as an age-appropriate necklace?) or shoes (that’s a project for another time). But I have a lot of work clothes to sort through, thanks to years of sample sales, outlet treks and hand-me-downs from my well-dressed mother. After many painful days of wearing clothes I felt unhappy in, I sold a dozen items at a consignment shop. I gave a bag of clothes to a friend who’s my size. I donated another armload to Goodwill. As the experiment continued, my colleagues and family started to demand a say.

“Keep it,” said the creative director about a vintage gold knit dress with tiny buttons. I did.

“Eh,” said the entertainment editor about a navy-and-teal Tory Burch dress. I sold it.

“Fabulous!” said the fashion editor about a lace bolero from my mother. In.

“Very nunlike,” said the executive editor about a cream silk Cacharel shirt. From her, a big compliment. In.

“Yuck,” said my son about a too-big color-blocked skirt from Etro. Out.

It’s weird having people vote like Caesar on your clothes—thumbs-up, thumbs-down, live or die. Still, I was happy when an old Pucci shirt looked fresh and when a gold wool skirt with sequins scored a “Chic!” from the fashion director. Things I wasn’t sure of on the hanger—like a blousy white Tucker shirt with metallic thread—suddenly made sense when I styled them with the right items. (“I love it!” said the beauty editor.)

Making my way through one rarely worn item after another, I started to think that if aliens beamed into my closet, they’d be convinced that several people used the space—and in a way they do: fossilized versions of me, over the years. But a closet isn’t a museum or an archive. It should be a simple storehouse of clothes that reflect who I am today and that I can wear to work tomorrow. I hated getting rid of a trashy black leather biker jacket that made me feel tough and rebellious. But that jacket doesn’t suit my life anymore, and I never wear it. I haven’t been to hear live music at a dive bar for years—hell, I haven’t been out past midnight for years. That’s why this experiment is sometimes painful: Letting go of clothing is letting go of who I used to be. Of course, that’s also the pleasure. How can we grow if we can’t let go?