THE WHOLE THING STARTED with my Courtney Love Halloween costume—torn Value Village lingerie, fur-lined burgundy coat, precarious and tractionless two-and-a-half-inch silver heels. When I slipped and took a nosedive down the stairs everyone applauded my rock ’n’ roll moves, but I wasn’t as hardcore as I looked.

I sprained my knee—badly—and would have to wear a brace for a month. While I waited for the brace to arrive, I spent my time working from home in a fog of painkillers, eating anything that came my way, watching the CW—in short, depressed. I looked forward to the brace arriving so I could leave the house and go buy those long, plaid wool skirts I’d been eyeing at J. Crew and get on with my life. I would coordinate the long-enough-to-conceal-the-brace skirts with a pair of leather riding boots, keeping a stiff upper lip in style. I imagined people saying things like, “Wow, Anna, way to make your injury work for you.”

The brace, when it finally arrived, was tight and stiff and ugly, made of black wetsuit material with menacing Velcro straps and strips of jointed metal running down each side. It smelled overwhelmingly of rubber. When I tugged on a pair of jeans, my leg looked like a snake that had swallowed a hamster. My upper lip wobbled, then collapsed. I burst into tears.

“It doesn’t look so bad,” my husband said. “Okay, maybe it does. But what can you do about it?” Besides refilling my Vicodin prescription and living on the couch for another month? Go shopping.

When I was a grungy teenager growing up in Seattle in the ’90s, I spent afternoons scouring the racks at Red Light and Goodwill, playing “find the perfect ironic T-shirt or the best-fitting pair of faded Levi’s.” I emulated the thrift-store cool of the local rockers I saw at RKCNDY and the Showbox: Isaac Brock, Elliott Smith, the Death Cab for Cutie boys. At college in LA, my grungy mountain-town style wouldn’t fly. My friend Kathleen, who grew up in Newport Beach, taught me rules no one in Ravenna had ever mentioned: A woman cannot survive without at least one pair each of black and brown heels. The pieces of jewelry you’re wearing should add up to an odd number. Your belt should always match your shoes. I ended up looking like Kathleen—a preppy girl from Orange County.

Back in Seattle for my first real job after graduating, I kept the striped button-downs and dress pants from Express, figuring even though I was younger than everyone around me and lived in a shabby apartment on Capitol Hill next to a drug dealer, people wouldn’t question me if I dressed the part of a young professional. The act worked, but sometimes I’d meet people I wanted to befriend and felt like screaming, “I’m so much cooler than this pink Ralph Lauren sweater!”

I had based my fashion choices on the assumption that, even in Seattle, it was a faux pas for a grown-up to wear sweatpants to a nice restaurant.

I saved my sartorial playfulness for costume parties and Halloween—which was how I ended up downtown on a rainy evening in muddy, baggy warm-ups over a bulky knee brace. I felt intensely uncomfortable among the designer-clad in Pacific Place, like a stranger in my hometown. Where was the girl who had once confidently worn T-shirts and ripped jeans? I was ashamed for being ashamed of my appearance. Disturbed by my vanity and subconsciously engaging in some sort of penance, I went straight for the sweatpants section in Old Navy, bought two pairs, and hobbled home to slump on the couch and watch another episode of The King of Queens.
The next day I had to attend a luncheon for work. I put on some sweats, halfheartedly dressed them up with a nice sweater and some jewelry, and approached the Icon Grill with apprehension, nervous I was breaking a cardinal fashion rule and would offend people with my impertinent legwear. Nobody noticed. I was practically dressed in pajamas and not one person looked at me funny. I apologized to the hostess, but she just laughed. “They look like nice black pants.”

For a month I wore sweatpants to Poco, Quinn’s, Ristorante Luciano, Café Campagne, the Brooklyn, the Cha Cha. I obsessed about my pants, but no one noticed a thing. I should have been relieved, but instead I was weirdly dismayed. I had based my adult fashion choices on the assumption that even in Seattle it was a faux pas for a grown-up to wear sweatpants to a nice restaurant. If I was wrong, what did that say about all the other rules I’d been imposing on myself for years? I felt untethered, unsure of who I was.

The night my physical therapist told me I could stop wearing the brace, a friend came over to 
celebrate. “That’s great,” she said, eyeing my legs. “So why are you still wearing sweatpants?”

She gently suggested I go change, and I went into my bedroom and stared at all those button-down shirts and professional-looking pants like I’d never seen them before. I’d forgotten how to dress myself, maybe had forgotten years ago. I pulled on my old favorite jeans and was startled to see the curves of my legs again. I slipped into an embroidered Indian top I’d always loved but rarely wore and added a preppy cable-knit sweater over it, layering my fashion history. I accessorized with a clunky necklace and dangly earrings, giving no thought to how many pieces of jewelry I was putting on, tucked a scarf through my belt loops, and donned a pair of sneakers that did not in any way match.

I turned to the mirror and glimpsed the girl I’d somehow lost in college, the one who had made choices based on what she liked, not what she hoped other people might like. Even though Seattle accepted me in sweatpants like it had accepted me in button-downs, I’d never felt like myself in either. Finally I was facing the image of someone I recognized from a long time ago: myself.

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