7 Shoes I've Had for at Least 3 Years (and Still Wear)

When I started working on this story, I was surprised to find that I didn't really have that many shoes older than three years that I still wear. I suppose I follow the trends and tend to grow tired of my shoes pretty quickly, which comes with the territory of being a fashion editor. Alas, I did discover seven pairs that are so classic I'm still wearing them years later.

So what are my criteria for shoes with longevity? It's pretty simple, but it depends on the shoes. For sneakers, I prefer clean, no-frills sneakers in black and white. For flats, it's loafers. For boots, it's Chelsea. And for heels, it's mules. None of these styles are going to become passé, they're all a little boring, and they're all casual yet polished. Keep scrolling to shop the exact shoes I'm referring to, and see how I style them via my Instagram.

Veja Esplar Sneakers

There are a lot of good white sneakers out there, but Vejas have been a longtime favorite of mine. They look clean, crisp, and classic, which is exactly what so many outfits need. (If solid white is too boring for you, there are plenty of options with a little more color.)

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(Image credit: @allypayer)

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ACNE Studios Jensen Boots

You've probably owned several Chelsea boots in your lifetime, as have I, but none that I've encountered have lived up to ACNE Studios' Jensen boots. They're basic but with some edge thanks to the graphic elastic detail and the metal-trimmed toe.

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(Image credit: @allypayer)

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Gucci Jordaan Loafers

Honestly, I think these are the shoes I wear more than any other pair. I wear them during the day, at night, to travel. I wear them with jeans, with dresses, with leggings. They're the most versatile, comfortable shoes I own, hands down.

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(Image credit: @allypayer)

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Nike Roshe One Sneakers

When it comes to athletic sneakers, Nike Roshe Ones have been my go-to the longest. They're simple, lightweight, affordable, and work equally well for workouts and running around.

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(Image credit: @allypayer)

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Mansur Gavriel Mules

Mules have long been my favorite heel style, and a few years ago, Mansur Gavriel made the perfect pair of kitten-heel ones, which I bought in camel grosgrain and black suede. I love the chic almond toe and how effortlessly cool they make my outfits look. Sadly, the style is no longer made, but I found a similar pair that are just as timeless.

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(Image credit: @allypayer)

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Madewell Elinor Loafers

Like I mentioned earlier, I'm a loafer girl. Before I invested in the Gucci style, I was partial to Madewell's loafers. This is the Elinor style, and they're insanely comfortable and classic.

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(Image credit: @allypayer)

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Vans Old Skool Sneakers

I first bought Vans Old Skool sneakers when they were the It sneaker a few years ago. Lo and behold, they're still cool and still worn by the most stylish celebrities (e.g., Hailey Bieber).

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Next up, 17 game-changing basics our editors can't stop wearing.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.