I Can’t Wear Heels

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and it tears me up inside!!!!!!!!!!!

On Friday I took a real lunch break to celebrate the incredible weather, doing that wide-eyed blinkey thing people who live on the garbage side of this planet’s hemisphere do when all the snow goes away and you’re really, really sure it will never come back, just like “ah sunshine,” faces tilted up like dumb little tulips. So I was out partially because of the weather and partially because I had ordered these shoes off The Internet™ from a mass-market mall brand that waives the shipping fees if you pick up the item in store which seemed like a responsible decision. The shoes are pretty cute, but honestly, the only reason I ordered them was because they were the only reasonably-heighted heels that came in my size. Do you know how rare it is to find heels in my size?!? For the record, I wear a size 5, yes I know that is cartoonishly small, yes I know it’s a miracle I can even stand upright, moving right along. Anyway, as soon as I saw the size 5 number I was like SOLD put these on my body immediately.

I have a Cool Wedding™ to attend in early June and the prospect of going in flats was weighing heavily on my tiny feet for a lot of reasons. First, I love heels the way I love all the most impractical kinds of fashion: recklessly, stupidly. Heels, when worn correctly, fake a kind of self-assurance and strength in their wearer. The sound they make!! The shape of your legs, elongated by a crisp point!! They connote power and they force a very unnatural kind of grace because every step matters so much. No one can forget they’re wearing heels while they’re wearing them. Heels encourage mindfulness. And, I mean, they just look fucking sexy. They’re gorgeous and terrifying, two qualities I’d most like to embody in my daily life.

But I go back and forth between two competing instincts: first, trying to make peace with the fact that I cannot walk properly in heels, and more than that, three hours in a pair of ill-fitting heels and the pain will turn me into such a monster no one will ever mistake me for a gorgeous boss bitch and just a red-faced menace, and that the beauty of heels comes from the confidence the wearer feels in said heels, and since I do not have that I just have to embrace cool flats or slight platforms with whatever of my dignity remains, and second, the completely irrational “but I’ll look so cooooooooooool” that echoes through my head when I hold a pair of really good heels in my equally tiny hands.

I have a really beautiful dress for this wedding, but it’s simple; My Look™ is going to be all about the accessories. So, getting back to the point, I ordered those dumb small shoes and walked to the store, headphones in, sunshine on my head, just daydreaming about how my entire life was going to change once I put these shoes on. Surely my previous issues with heels came from the size, not my own confidence issues; trying to fake my way into a size 6, typically the smallest size manufactured in North American shoe markets, had been my downfall (literally) (because I fall when I wear shoes that are too big for me) (you get it). I walked with the kind of stride I imagined I would feel when these perfect shoes would be on my feet and did that thing where I impulsively stopped into a store wearing one pair of sunglasses and walked out wearing a completely different pair (plus a new purse, lol) because I was just having a GREAT DAY.

Let’s back up for a second so I can talk to you about why these shoes were so important.

For the last few years, I have played an incredibly fun and thought-provoking game with some of my friends: it’s called “What’s Your Look?” As the name implies, the question requires a single answer that encapsulates the references, inspirations, aspirations, and effect you hope your seasonal look will communicate to everyone who looks your way. We play this game right as the seasons change: What’s Your Summer Look, What’s Your Fall Look, etc. I like to turn it into a story with a character, location, and conflict, but that’s not entirely necessary. As an example, my Winter Look was “recently divorced mom [see: Alicia Florrick] goes on ski weekend with the friends she lost touch with while her marriage imploded.” So, like, light blue jeans, big hiking boots with red laces, big knit sweaters in neutral colours, huge soft scarf, slightly messy hair, tasteful and minimal gold jewelry. When I explained this look to Jazmine she was like “why does the mom have to be recently divorced” and I said it was because that would make her prime for a sexual reawakening and I’m pretty sure that’s when she was like “I quit.” BUT I DIGRESS.

My Summer Look, on the other hand, started off slightly simpler: Slutty Babysitter. So that consists of: ripped up denim shorts, bratty band t-shirts, sneakers, big gold earrings, even bigger blonde ponytail, big aviator sunglasses. Some real “light of my life fire of my loins” shit tbh.


But now that I had the prospect of these heels in mind I started to waffle. As any reasonable person knows, the ultimate style/life role model is Alicia Florrick; she is the person I’m thinking of when I think of someone who commands attention in a pair of heels. I recently bought a purse just because I thought it was something Alicia Florrick would carry, and then shortly afterwards returned to the same store to buy a pencil skirt that should have been called “The Alicia” because it was just that perfect, and I started to wonder what Alicia’s summer look might be. Pencil skirts and tasteful t-shirts in soft silky materials, maybe? Of course, the first time I wore the pencil skirt I ripped it within 2.5 hours, and when I took it to my tailor she was so horrified by what I had done to the seam she asked me what had happened, and the truthful answer was something that I’m pretty sure Alicia Florrick would never do outside of the smutty fan fiction I plan on writing later this summer when I have more free time, so I just shrugged and threw some money at her and ran back to my originally planned summer look.

Here’s where my new story started to take shape as I walked down that very busy street on that very beautiful day. Slutty Babysitter Trying on A Cool Mom’s [see: Alicia Florrick] Accessories While The Kids Are Downstairs Watching Frozen For The Millionth Time. So that way I can incorporate all the big pearl earrings and rings I’ve been buying recently and the new purse I had just foolishly purchased, and of course the heels as well, you see? You see.

When I got home I put the heels on immediately, and praise hands emoji, they fit perfectly: a Good Wife-inspired miracle. I walked around and took a bunch of selfies to send to my friends and fans (thanks guys you give me strength) and felt a deep sense of peace knowing that my Summer Look game was, as always, extremely strong.

Then I decided to walk to the restaurant two seconds from my home to buy a $13 salad while wearing the shoes.

It took me twenty minutes to get there and back.

What the fuck. What is this mental block stopping me from achieving my true goals both in fashion and in life? Because if it’s true that heels give their wearer power and gravitas, the opposite is equally true: watching a person walk in heels when they aren’t comfortable in them is like watching a very uncool deer take their first lame steps.

The walk back from the restaurant was far better than the walk there, and on the smooth surface of my apartment floor I felt fine, but the unpredictable sidewalk felt impossible to navigate, and my entire body felt like it was going to snap my dumb small ankles with every step.

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So, back to the drawing board with the look, I guess; just your run-of-the-mill babysitter running around in Converse or some similar sneaker. I will continue trying to cultivate some kind of impressive confidence in flat shoes. I am going to wear these shoes to the wedding and just hope it’s not one of those standing ceremonies; will also probably hide a pair of flats in my purse because I’m weak and terrible at being a Grown Woman.

Do YOU wear heels? CAN you wear heels? If so, is there some secret to it that I’m missing, besides wearing heels that actually fit? Do you want to see some of the selfies I took when I was wearing the shoes at home? Get @ me with your answers in the comments please.