Shoes and the City (Or How I Stopped Trying to Be Carrie Bradshaw)


Do you remember where you were when Sex and the City premiered? I do. I was watching Walker, Texas Ranger — #NoJudgment — with my parents, a/k/a still living that virgin life. I was fourteen years old, you see, and the last thing my parents wanted was to have cable and for me to get ideas from racy shows like HBO’s SATC and its four fictional women — Carrie Bradshaw, Samantha Jones, Miranda Hobbes, and Charlotte York — and use those ideas to cash in my virginity like it was some Dunkin’ Donuts gift card. So with no risqué TV as a source of inspiration, my factory seal remained intact and I lived out my high school years in Cleveland pretty uneventfully. I did extracurriculars like mock trial, hung out at Panera Bread, and maintained my status as the funny but perennially single gal.

In my mind, I blamed my singledom on the fact that my private Catholic prep school was devoid of Scott Speedmans and Scott Foleys (the hotties from Felicity), but if I’m being honest, it was because of my wardrobe. My outfits screamed Diane Lane in the first fifteen minutes of a romantic comedy: baggy button-down shirts, cable-knit sweaters, pleated khakis, and…turtleneck dickeys. I know. But it’s not my fault. It was the late Nineties/early Aughts, the era of flare-legged denim and boys getting all Moses-like by parting their hair down the middle like Home Improvement‘s Jonathan Taylor Thomas, so a little turtleneck dickey action is forgivable. Right? Well, it happened. I wore these dickeys and I looked fifteen going on forty-five and working in Accounts Payable. Thankfully, my saving grace came in the form of my age-appropriate shoes.

I wore chunky-heeled, platform oxfords because Brandy did on Moesha. My Mudd-brand penny loafers were my go-to when I wanted to feel “Annie, are you OK, are you OK, you OK, Annie,” a/k/a serious AF like a Michael Jackson video. And when I wanted to show I’m hella casual, like a white dude wearing flip-flops in winter, I put on my Skechers platform sneakers, which were my tribute to Baby Spice. (In case you were wondering, my homage to Scary Spice is my brown skin. Duh. Zig-a-zig-ah!)

Anyway, I felt pretty confident I was nailing it. So I packed all those shoes in a suitcase and headed off to college at the Pratt Institute in Brooklyn. And then I got here and…saw what real New York women were wearing. No Mudd loafers. None.

It was stiletto heels, all day, e’eryday, y’all! Women wore them to the grocery store, on the bus, at the bank, and probably while in stirrups at the gynecologist’s office just so their calves could look a skosh more amazing while lying down. I guess Oprah should’ve been more specific when she instructed us to “live our best lives.” Anyway, my chunky shoes made me feel like I was Hicksville, U.S.A. Well, fuck this, I thought, I’m not going to turtleneck-dickey my way through college. No siree, Bob. This is going to be a new Pheebs.

So I started doing research and bought my very first fashion magazines. I scoured the pages of InStyle, Vogue, Essence, Marie Claire, and Glamour hoping to get some guidance. Unfortunately, there were no style tips like “Sure! Wear those comfy platform sneakers. Who cares that they look like someone hot-glued a block of uncooked cranberry sauce to your feet?” Instead, I saw photos of Cameron Diaz, Halle Berry, and Catherine Zeta-Jones wearing the latest fashions and sleekest shoes. Hmm, I don’t look like them. I mean, I got into comedy and writing because I’m not a perfect ten. So…. Time for a new source of inspo — cable TV!

Usually I just watched HBO at night to get my fix of Real Sex and Taxicab Confessions, but one afternoon I was pumped up on Benadryl to fight off an allergy attack and flipped over to the channel. I had no idea what I was watching. I just saw this Carrie Bradshaw woman, narrating her life, dating a cute guy named Aidan, and wearing stiletto heels. Hmm. Seeing Halle Berry in heels might have been discouraging, but seeing Sarah Jessica Parker in them felt attainable. After all, she was a writer, didn’t look like a supermodel, yet gracefully leapt over puddles in the heels (only later would I learn that Parker studied ballet when she was younger, hence the gracefulness). I was transfixed.

Hell, all my girlfriends were. We’d catch up on the show via reruns until we were watching the final season in real time. We’d talk about Louboutins and Jimmy Choos, ooh and aah over the latest Cavalli outfit Carrie sported. I know this may seem like a cliché now, but I really, truly mean this: For women of a certain age, Sex and the City was a blueprint for how to be an NYC woman. It presented a fantasy New York that was clean, a place where you can have brunch with your gal pals all the time, date hot dudes, and look amazing every second of the day. Who doesn’t want that?

So we emulated the SATC ladies by starting at ground zero: our shoes. My platform sneakers and comfy flats were tossed in favor of high-heeled leather pumps from Nine West. As soon as I saved up enough money, I bought chocolate-colored thigh-high stiletto boots from Cole Haan. They were no Jimmy Choos, but like Carrie Bradshaw, I would wear them on a fall day, walking around town.

To clarify, I was actually walking and complaining around town. What Sex and the City doesn’t tell you is that wearing four- and five-inch heels all day fucking hurts. They may be beautiful and turn the heads of women and men who are in awe of you prancing like Seabiscuit. But. They. Fucking. Hurt. Stilettos pinch your toes, have negligible arch support, and force your feet into uncomfortable positions. I mean, they are so evil that even Satan would be like, “Ease up, fam. Take off those heels, put on a sensible shoe, and for God’s sake, use a Dr. Scholl’s gel insert.” And you’d be all like, “Aww,” and then the Devil would impregnate you with his spawn. But for those thirty seconds when you’re just chilling in Aerosoles, you’ll feel like you’re in heaven, which for me is being knighted by Michael Fassbender’s peen. #NoJudgmentTheSequel.

High heels make you late for business lunches, meetings, the subway, etc. They’re impossible to run or make any sudden movements in without tripping like a white girl in a horror movie. And worst of all, stilettos run down quickly because we walk everywhere in NYC on streets as uneven as British teeth. Case in point: My Cole Haans lasted one season before the heels were destroyed and I’d need to have them patched up by a cobbler, which I never did because fuck cobblers. Nothing against cobblers, but did I fall asleep and wake up in Colonial Williamsburg? No? I’m still in the present, where the word “cobbler” is mostly used in reference to the pie and black people have their rights? Great. That’s the world I want to keep living in.

But before you think this is an “everything that is wrong with the world is represented by stilettos” rant: It’s not. I still love them and lust after them when I’m window-shopping outside Prada. But I am a thirtysomething freelance writer and stand-up comedian. It’s my job to stand onstage for twenty minutes at a time, telling jokes and making strangers laugh. It is my job to be relatable to audiences and do anything in service of the joke — like hump a stool. I can’t do that if I’m worried about twisting my ankle. That’s not relatable. That’s high-maintenance. That’s me continuing to live in the fantasy of a nonexistent NYC, as opposed to living in the reality of the NYC that is my home.

This real New York City is messy, complicated, fast, stressful, exciting. So I wear more comfortable and less trendy shoes, like my Converse sneakers or Nike wedges or a bootie with a kitten heel. And that doesn’t mean that I’m turtleneck-dickeying my way through life. I’m still stylish. I’m still leaping over puddles à la Carrie Bradshaw. The only difference is that when I land, I’m no longer going, “Shit, that hurt my ankle and I just missed my train.” Instead, I’m landing with grace and I still have time to run and catch the A — where I will have to stand the entire ride, because that’s the other thing Sex and the City doesn’t tell you about. The trains are crowded as hell here. But still, NYC is fabulous.


Phoebe Robinson is an NYC-based stand-up comedian, writer, and actress. She is the co-host of WNYC’s 2 Dope Queens podcast and her debut collection of essays, You Can’t Touch My Hair, will be published by Plume books in the fall of 2016.

[This is part of the spring 2016 edition of Sheer, a quarterly style supplement by the Village Voice devoted to exploring and sharing the most dynamic elements of New York City’s fashion and design worlds, from the iconic to the as yet undiscovered. Check out the rest of Sheer’s featured stories here.]