The Item I Wear to Death: My Black Canvas Toms

I've worn them for all occasions, from work to weddings.

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In our biweekly series, our editors will be sharing "the item they wear to death," whether it be a basic white tee or a super-trendy jumpsuit. Prepare yourself (and your credit card) for some guilt-free shopping.

I did not grow up in a household obsessed with designer labels. I learned early on that Fruit Circles and Froot Loops were the same thing ("they're made in the same factory," my mom would explain, "they just put some of them in more expensive boxes") and that buying anything that wasn't marked final clearance was reserved for chumps. My family's off-brand only, deep discount-loving attitude, naturally, extended to my wardrobe, which consisted mostly of clothes my grandma picked out for me at yard sales and me buying graphic tees from Walmart's clearance section.

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Me, age six-ish, in a pink, tie-dyed Troll sweatshirt, white sweatpants, white socks, and white open-toed plastic dress shoes. The entire outfit probably cost about $1.75, but the pictures are priceless.

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This was more or less how I acquired clothes and dressed myself through high school. I was exactly as popular as you're imagining and, sure, in retrospect, it may have had something to do with my wardrobe (I did not give in to the ever-so-slightly-too-tight Abercrombie & Fitch t-shirts and chunky blonde highlights, which were all the rage but definitively not my style). I, however, never really stressed about that. In fact, fashion meant nothing to me until I moved to Los Angeles and got my first job at a national magazine, where the official dress code was, and I quote, "casual-trendy-cute."

So, not long into my L.A. tenure, while walking around a mall with two friends who actually went to malls to shop and not just to see how many Auntie Anne's samples one can get, I splurged on my first-ever pair of "name brand" shoes: Toms.

Okay, so this wasn't exactly a Carrie Bradshaw moment. But, spending $50 on a pair of shoes went against all the values I learned in my upbringing (even if I could pretend it was kind of like spending $25 because the company promised to donate to charity as a result of my purchase). Despite this minor guilt-ridden moment, it was love at first slip-on. (I knew the way you know about a good melon, if you will.)

My first pair of Toms was not the black canvas style that has since become my signature. They were sparkly and covered in glitter and I bought them because they reminded me of The Rainbow Fish

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I regret to inform you that these are now discontinued. RIP, galaxy glitter Toms.

(Image credit: Toms)

I wore that first pair of Toms for about a year, until they were coming apart at the seams and smelled truly awful. It took all my strength to throw away the most expensive item of clothing I had ever bought for myself. And, even more to resist the urge to buy a pair of cheaper "Bobs" instead of shelling out again for the shoe I really wanted.

Fast forward six-plus years later, I now replace my Toms like clockwork every six months. Sometimes even sooner, because when you wear them every day for every activity, they wear out pretty quickly.

The shoes are worth it, worth every usually-pinched penny. They are comfortable. They slip on. When you break them in, they feel almost like they're formed just for your feet...or they do for me anyway.

Plus, now that I'm buying them in black and not rainbow glitter, they're also appropriate for just about every occasion. I've worn them on interviews, on roller coasters, on subways, and on dates. I've worn them with jeans, with shorts, with dresses, and with skirts. They might not be the right shoe to wear to certain fancy-schmancy events, but they also never look totally wrong anywhere. I've never felt embarrassed about my Toms and I've never felt either over or underdressed in them, either.

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Me getting fro-yo in my Toms. It was a good day.

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Do you want your own pair of magical, slip-on, go-with-everything, are-at-least-vaguely-appropriate-for-every-situation shoes? Shop them, below.

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Weekend Editor at Cosmopolitan

Kayleigh Roberts is a freelance writer and editor with over 10 years of professional experience covering entertainment of all genres, from new movie and TV releases to nostalgia, and celebrity news. Her byline has appeared in Marie Claire, Cosmopolitan, ELLE, Harper’s Bazaar, The Atlantic, Allure, Entertainment Weekly, MTV, Bustle, Refinery29, Girls’ Life Magazine, Just Jared, and Tiger Beat, among other publications. She's a graduate of the Medill School of Journalism at Northwestern University.