A decided non-clotheshorse reflects on school uniforms, a crazy skirt, and the notion of ignoring price tags.

When I was a kid, my mother owned one dress. I can still picture it: solid forest green. Boxy, knee-length, short sleeves. No embellishments; nothing remarkable about it. As a piece of clothing, it wasn’t fancier than any other item. It only happened to be in the shape of a dress that made it acceptable for her to wear it for every occasion: church, someone’s graduation, a holiday party. Year after year, out came the dress.

In our traditional family in the suburbs, my father earned the only income. My mother stayed at home and took care of the four children. Instead of buying dresses, she fed us. Dinner might be barley with bits of sausage. Or rice pudding with raisins. Leftovers night meant mysterious crumpled pieces of foil—unraveled, they revealed shriveled hunks of unrecognizable meat.

The money, apparently, was spent on tuition for private Catholic schools where my siblings and I were sent. For eight years of grade school, I wore the plaid wool jumper of St. Catherine’s: blue and gray, with knee socks and saddle shoes.

In high school, an all-girls college-prep that no longer exists, we wore white blouses and sky-blue pinstriped skirts. Thus outfitted in downtown Silver Spring, Md., blocks from the D.C. border, we’d commonly get propositioned by men on the street. Driving by, slouched at the wheel, they’d offer a ride, eyes on our legs. Other teenagers wore whatever was in season. We wore skirts. I didn’t choose my clothes each day. Or any day, for 12 years.

Fast forward 10 years and 3,000 miles from the East Coast to the West. I arrived to the Reggae on the River festival clad in cutoff jean shorts—appropriate attire for a hot summer day in much of the country. But this was Northern California, at a reggae festival. Revelers wore African prints or the familiar motif of red, yellow, green, and black. Happy people surrounded me, expressing themselves through their garb.

I hung back, on the periphery, observing. And then I went shopping. Perusing the booths, I found a crazy skirt. Or it found me. A flashy batik of blue, green, and purple, it flared with pointy ends, like an inverted joker’s hat. It flew as I spun. Flew with abandon. Wild and free. Ditching the cutoffs, I returned to camp. The skirt steered me. I was energy. I was color. I danced and the pointy ends floated with the music. Later, walking to the river at dusk, my friend Bonnie said, “This whole event changed for you when you bought that skirt.”

Growing up, I didn’t get practice at buying clothes. I had no need, my body trapped in uniforms. My nonschool garments were pretty much hand-me-downs from my older sisters. And with my allowance and gift money from birthdays and Christmas, I saved up for horseback riding lessons and gymnastics classes. To buy clothes never occurred to me. Never. In high school, with my best girlfriend, not once did we go shopping for clothes. Not once. The shopping gene skipped me entirely.

And it showed. Jump forward another 10 years, to Colorado. As a server in a brewpub, I wore my blue jeans until the cuffs frayed and the butt thinned to invisible.

The owner stopped me one day and asked if I liked the job. “I love it!” I replied.

“Do you make enough money here?” he said.

“Yes, of course!” I answered, clueless to his point.

“Great,” he said. “Think you could invest in a new pair of jeans?”

At the time, my budget—and my tolerance for shopping—stretched far enough to secure the necessities for my lifestyle: cycling and ski gear. Even then, for warmth in the snow I relied on wool pants and sweaters from thrift stores. It’s not that I disliked fashion. I just found it hard to spend the equivalent of a month’s rent on a stylish outfit.

Another decade passed. Now in Oakland, I need to suit up for a job interview. But since I’ve neglected to acquire a go-to green dress, I find nothing sufficient in my closet. T-shirts from KALX—UC Berkeley’s community-run radio station—have taken over, choking my wardrobe like ivy. In awe, I count them: nine shirts, a different design for each annual fundraiser. Not even the one signed “You Rock!!” by DJ Cuppa Joe will cut it for the interview.

Of the many ways I’d allocate my winnings if I won the lottery, here’s a plan for the honeymoon period: I’d walk into a chic boutique, maybe a small storefront on College Avenue. Or a high-end department store, say Saks Fifth Avenue on Union Square. I’d try on whatever clothes suited my mood. If they didn’t exactly fit, no matter: I’d have them altered. I’d pick out pants, tops, a jacket, even a dress. A whole outfit, head to toe. I’d get some really cool boots. And in my lottery-winning fantasy—as I strolled through the store choosing whatever chose me—not once would I check a tag for the price. Not once.

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Kathy Hrastar is a freelance journalist and waitress in Oakland who keeps busy biking around town and dragon boat paddling. She still has the skirt, which made an appearance at Burning Man, and her essays have appeared previously in The Monthly.