I’m thirty-eight now. For my sister, fifteen years older, this bit of news hit hard. It seemed more upsetting to her than when she herself turned fifty, a milestone she passed with trademark grace. “But I was thirty-seven for a whole year, and that didn’t seem old.” I pleaded. “No.” She stood her ground, “You’re old now.”

And so I am, quite suddenly, old. At my birthday party, I felt punchy, liberated even, as I developed for myself the catch-phrase: “I’m pushing forty! I do the fuck I want!” It turns out this catch-phrase is limited in both application and enduring charm. But it does express a certain sense of relief I feel having made it to middle age. Cause let’s face it, given certain lifestyle choices on my behalf, I’m definitely there.

Sometimes people wait until they are actually elderly to stop caring what other people think. Since I’ve only ever marginally given a crap, it’s just taken the tiniest nudge to push me into all-out apathy. One of the things I don’t care about because I’m so fucking old is certainly what the fuck I wear.

Again, this has never truly been something I worry too much about in terms of “public opinion”. But let me clarify:  I care very much about my appearance when it comes to prospective employers, prospective boyfriends, friends who are more hip than me, and the parents of my children’s friends. The rest of you all can suck it. To whit: I just went to the corner grocery store in pajama pants, a tank top that highlights my mooshy mid-section, a scarf that is part of a child’s pirate costume worn as a do-rag and a men’s cardigan from 1984. (acrylic, navy) And you know what? The clerk who works six days a week because he is single (wink), and doesn’t have anything else to do anyway as he kindly informed me, kind of hit on me.

Throughout my life, like many misguided women of my generation, fashion has played a major role in defining my identity. Just in case you’ve only known me for two weeks, let me offer you a brief history of some of the highs and lows along the way:

K-8: She’s so unusual
My mother not only let me dress myself, but never even offered an opinion on the whack shit I left my house in. I wore fake leather pants in fourth grade for God’s sake. And because I lived in an insanely homogeneous small town with no mean rich girls to make fun of me, I really had no idea what a freak show I was becoming. In my defense, it was the eighties. My fashion idols were, duh, Madonna and Cyndi Lauper. Having no access to clothing stores or the money to use at them, I raided my mom’s closet hand-me-downs, and a trunk of dress up clothes in the basement. The result was a midget-sized cross between Murphy Brown and Shelia E.

Highschool: Every day is Halloween
A crucial event between eighth grade and my freshman year was Art Camp. I smoked my first cigarette, met a boy who skateboarded and was introduced to Suicidal Tendencies. Also I met punk rockers from Madison.  I had packed every Forenza t-shirt and Esprit bermuda shorts in my collection, only to meet girls with shaved heads and combat boots who knew how to use blow torches. I returned to Hartford with a new bad habit and a head full of bad fashion ideas. Like torn  tights worn under jean cut-offs, or worse yet, long underwear under boxer shorts.

Thankfully I was delivered via Angie, my goth friend with access to and knowledge of the Army Surplus store on Wisconsin Avenue, and Sweet Doomed Angel, a vintage boutique on the East side of Milwaukee. Then there was Chris, my then-closeted gay friend, who became my own personal Tim Gunn. He could be cruel to be kind. He took me shopping for my prom dress, and actually blushed when I came out of the dressing room with decoletage, God Bless his queer heart.

I was, in fact, surrounded by like-minded, equally daring dressers. Each of us had our own signature – Jenny for example, favored hats neatly propped behind a massive wall of blonde bangs. Danielle did this thing with safety pins and the collars of men’s shirts… it’s hard to explain. But it looked cool! One thing we all had in common, as girls growing up in the eighties, was: at all costs obscure your killer bod. Giant, David Byrne like suits or men’s vintage shirts would mask any semblance of a breast. Youth, again, wasted on the young.

Personally, I settled into a new wave thing for most of high-school. I had a platinum bob and my style was not unlike Winona Ryder in Heathers. Lots of colored tights. It held until senior year, when I began to smoke pot, or at least pretend I did, and decided to become a hippie, or something. Things went downhill fast.

College: Rings on her fingers and bells on her shoes
Once I realized that head shops not only sold drug paraphernalia but also clothes and jewelry, it was over. So over, my friends. I wore Birkenstocks to the exclusion of all other footwear. Flannels, Guatemalan pants, and t-shirts ordered from the Wireless catalog – all at the SAME TIME. And weight gain. Dark times for this Little Wing. Thankfully I remember almost none of it. Except for my very expensive education which has been invaluable in too many ways to mention, Mom.

Twenties: Ballad of a ladyman
The first step to recovery is admitting you have a problem. The second step is to make a past-time out of shopping at the myriad kick-ass thrift stores of St Paul. Throughout my twenties I careened between ‘actually-sort-of-hip’ to ‘trying-a-little-too-hard’ to ‘what-the-hell-is-she-wearing-now?’ This was when I first heard people say to me: “I could never pull that off.” to which I might have answered “What? The cat-eye glasses, platform shoes or lavender pedal pushers?” I’m not joking. Look up tragically hip in the dictionary and I am cited. I had black hair with short bangs bla bla bla. Google Sleater Kinney. Next!

Thirties: Crossroads Blues
When I speak of the Crossroads, I speak not of the fabled place where Robert Johnson sold his soul to the Devil, but rather the horrible Crossroads Mall in St Cloud Minnesota. Shudder. Three important things happened during my thirties, fashion wise:

1. I had kids. For at least a year I really didn’t care what I was wearing as long as it was washable. My kids spit up so much I thought I’d never wear black again. Then, when I started to wake from the newborn-induced coma, I realized I hadn’t gone shopping in two years. Which leads to number 2.
2. I lived in St Cloud. The best dressed women in St Cloud shop by mail order, or drive to the cities. The shopping mecca of St Cloud is the Crossroads Mall, which is peppered with overpriced stores that cater to the tween and/or slut set. So instead I culled a weird wardrobe from the insane clearance racks at Herberger’s and the local Savers which is unparalleled, in my opinion.
3. I got a professional job. This job required me to appear, well, professional. Since I was a “Creative” (yes, that passes for a noun) I could get away with more than you might expect. Like pigtails. But sometimes they let the Creatives (monkeys) out of the cage and we had to go meet clients. It turns out I look like a midget when I wear a suit. Wrap dresses for every season ladies! Also I wore neck-ties because they are, and will always be, sexy on women.

Forties: Black to the Future?
In my late twenties, out of boredom, I formulated a plan that when I turned forty I would wear only black for a decade. I think I was trying to be original, or funny, or maybe I just am really that weird. In any case, the closer I get, the more my closet is trending in that direction and I think it isn’t a half bad idea. Except that I actually like color. But at least I no longer try to get away with pigtails (very often) or child barettes (hardly ever) or costume jewelry (only for parties and sometimes the gay bar). And I almost never wear age-inappropriate retro t-shirts or vintage skirts that look A&W uniforms. But when I do, I rock it, because you know why? That’s right: I’m pushing forty, I do the fuck I want! See it is catchy!

Author’s note: I’m forty one. I let my hair go grey, and I look more and more like David Lynch (in a dress) every day. Perfect.