I Tried On 8 Espadrilles for My Next Vacation, and These 5 Were the Most Flattering

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(Image credit: @_sierramayhew)

Buying shoes online has never been easy, but thanks to our associate fashion editor Sierra Mayhew, now it is. She zips around the stores of New York City trying on every trending shoe to report on the comfort, fit, and style so you never have to make a return again.

If you've read my column, you know I am a sucker for a comfortable pair of shoes. I mean, I started If the Shoe Fits because I refuse to settle for anything that I can't walk my 10,000 steps in. So with that being said, it was a natural journey for me to focus on a very specific shoe style for my summer wardrobe. Who doesn't love espadrilles when the weather begins to warm up?

Spotted on Anna Wintour on a nearly weekly basis and also Kate Middleton, this shoe style is perfect for any glamorous person who also flirts with the idea of keeping it casual from time to time. I can guarantee all the styles I tried below are comfortable, as that's just the nature of espadrilles. Not only that, but I was impressed by the fact that everything was pretty much sized as I expected. There were no returns or exchanges here. Below, shop the five espadrilles that I'll be raving about and that I'm sure will sell out by summer.

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(Image credit: @_sierramayhew)

When I first began my search for the best espadrilles, this style from Tory Burch instantly grabbed my attention. Designers have been selling everyone on the timeless thong sandal, and this might be my favorite pair to date. They look so luxe for a great price, and I can tell you that in person, the quality is just as good. I love the ankle strap because it makes me feel secure in these shoes, and they're more comfortable than the other thong-style sandals that I've tried.

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(Image credit: @_sierramayhew)

Of every style that I tried today, this was the most comfortable. For some reason, Zara's shoe section often exceeds my expectations, and I tend to walk away with a pair of shoes that I can wear anywhere I go and still be comfortable. At under $100, this is my suggestion for anyone who is on a budget but determined to wear a pair of espadrilles.

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(Image credit: @_sierramayhew)

As soon as I tried these shoes on, I decided that they are perfect for an outdoor wedding. Skip the stilettos that will have you sinking into the sand. The sole of this shoe is solid, and you'll avoid taking a tumble. Any event on your calendar will be a great fit for these shoes, and I highly recommend wearing them wherever you're headed. This style reminds me of the YSL Marrakesh store that I'm dreaming of visiting.

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(Image credit: @_sierramayhew)

When I started working on an article about espadrilles, I became interested in the history behind them and learned that Yves Saint Laurent himself called upon Castañer, a Spanish brand that invented wedge sandals, to create the first style that Saint Laurent would produce. If you know espadrilles, you know about this brand, and you can trust that anything you order from it will be good. I love that leather and canvas play together in this pair to create a beautiful woven point at the toe. It's a luxury take on flats that I'm absolutely here for.

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(Image credit: @_sierramayhew)

These shoes are so sleek and structural that at first sight I was nervous to put them on. In all honesty, they look a bit uncomfortable from afar. As soon as I slid them on, I was convinced that they are the best shoes on the market if you're looking for a pair of espadrilles that feel modern. The wedge on them was quite sturdy.

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Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.