At What Age Can I Go Back to Dressing Like a Lunatic?

(Graphic: Kat Borosky/

My first fashion-related memory is of my dad taking me shopping for my first pair of glasses. My mom — perhaps unwisely — had opted to stay home. I was 4 years old and had already developed a magpie-like obsession with anything shiny. So I immediately honed in on a pair of purple, rhinestone-encrusted cat-eye glasses, the likes of which had not been in style for decades.

I was utterly enthralled by the sparkles that dusted every angle and the pearly purple plastic that framed my face so glamorously (I thought). My goal in life at the time was to be “fancy,” and I used the word constantly. And to me, those glasses were the fanciest fucking things I’d ever seen.

My mom was not thrilled that her small child came home looking like a trashy, cross-eyed secretary, circa 1952. I didn’t care that she was mad. These glasses made me “fancy.”

My next fashion-related memory is more utilitarian. It’s of being outfitted for the uniforms my siblings and I were required to wear to St. Thomas the Apostle school in Rochester, New York. The uniform was a textbook wool tartan jumper with a Peter Pan-collared blouse worn underneath.

Though I loathed our uniforms, having zero in the way of outfit choices certainly did eliminate the guesswork of getting dressed in the morning. But that all changed when I was 12 and we moved to New Jersey, where I attended public school.

I had no idea what I was in for. In New Jersey, nobody was wearing bell-bottoms anymore — they were all about the straight leg! My mom didn’t understand why I suddenly needed Levi’s and that none of the cheaper options would do.

I spent three years desperately trying to fit in, spending all my babysitting money on Fair Isle sweaters, Lacoste polo shirts and Bass Weejuns, and yet no matter what I wore, I always felt like an imposter. Dressing like the popular kids didn’t make me popular, it just amplified our differences. One day it occurred to me that I didn’t actually like wide-wale corduroy — so why on earth was I wearing it? In fact, it was that pair of atrociously ill-fitting tan corduroy pants that convinced me to say, “fuck fashion.”

Well, that and the Sex Pistols.

I gave my preppy clothes to my sister and started dying my hair. Instead of shopping at the Gap, I haunted vintage shops, snatching up mohair sweaters and sequined skirts. I still remember the thrill of going to Trash and Vaudeville in the East Village to buy my first pair of super tight black jeans. As I nervously walked out of the dressing room to show my friend how they looked, the tattooed sales guy looked me up and down and declared I needed a smaller size. I just about fainted with pride. Shopping at Lord & Taylor never gave me this kind of a rush.

And for the next 20 or so years, I hung on to some variation of this tough chick look; though gradually, and reluctantly, I started to morph into a more grown-up dresser. Out came nine of the 10 piercings in my left ear. I gave up on the nose ring some time in the ’90s. The mohawk grew in, and midway through the aughts, with the help of my hairdresser, I transformed my fire-engine red, or teal, or green, or blue-black hair into a more tasteful chocolate-brown. Though I still love a bargain, bedbugs have scared me out of thrift-shopping and besides, most of the “vintage” stuff in there is the same stuff I rejected in the ’80s the first time around.

These days, I have corporate clients and have revamped my wardrobe accordingly. Instead of band T-shirts, I now wear tasteful dresses from Boden and cashmere sweaters from J. Crew. I still wear skinny black jeans, but now everybody else does too, so I don’t have to trek to Trash and Vaudeville to get them. My hair is a fairly normal looking blonde and the other day, a friend noticed it had a hint of pink. She told me it looked cute. I disagreed.

The subtlety of the tint annoys me because if I wanted pink hair (which I do!), it wouldn’t be a pastel, it would be a loud, proud, fuchsia. But I can’t have hot-pink hair because I’m stuck in that dreary, no-woman’s-land between middle-age frumpdom and old-lady eccentricity. Lynn Yaeger, Isabella Blow, Daphne Guinness and Vivienne Westwood can pull off all kinds of crazy shit because they either work in fashion (or worked, in Blow’s case) or are loaded or both.

Maybe if I win the lottery or my next book sells a million copies, I’ll feel free to let my freak flag fly unfettered. But at the moment, I feel like I need to wait a few years until I can pass my preferences off as eccentricity. But you can bet, the day I turn 65, my hair will be cobalt, my sequined Mrs. Roper caftan will be in full effect and I may even rock a jeweled turban.

Tell Us in the Comments

What do you think?

4 Responses

  1. Kiki

    as long as you don’t look like a week old cibatta, you’re doing good. fuck clothes, it’s all in the attitude and the number of cats you can amass anyway.

  2. Lee-Anne

    I’m already planning my 65th “Iris Apfel” coming out party. As of that moment I will wear what I want, where I want and when I want and you, are all invited.

  3. Ann

    In the 80s when i was at scool i use wide wale corduroy, mom allways buy me that. But it was fashion on that time.

  4. Editor’s Note: Perfect At Every Age | Tue Night

    […] Judy McGuire holds off the Mrs. Roper caftan. […]


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