I Tried On 8 Espadrilles for My Next Vacation, and These 5 Were the Most Flattering
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.
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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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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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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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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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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A dupe of Anna Wintour and Kate Middleton's favorite flats.
Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. 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. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.