You Won't Regret Packing These Stylish Shoes for Your Next Vacation

Sponsor Content Created With Sperry

With so many friends sharing stories about airlines losing their luggage, I've become a firm believer in the carry-on suitcase. Last summer, I managed to pack for a two-week vacation (for two very different cities, might I add!) in one small bag, and I've been on a roll ever since. But that means I have to be very particular about what comes with me. I'm always on the hunt for pieces that can be worn multiple ways because I'll likely have to repeat a few throughout the trip. (Sue me.) So I was super excited to hear from three fashionable frequent fliers (who you likely already follow on IG) that Sperry shoes were on their list of must-pack items this summer for this very reason. And after seeing how they styled them, I'm more than ready to throw any of the below pairs in my suitcase for my next getaway. Curious to see what I mean? Keep scrolling.

Paloma Meehan, Content Creator


(Image credit: @palomameehan)

"These shoes are perfect for vacation since they're neutral and go with the majority of my closet! Sperry shoes are so cute and easy to wear with any minidress, maxi skirt, or your favorite pair of jeans. They have a classic and timeless style that has remained popular for decades, so they're always in fashion and can be worn year after year without looking outdated (which is truly why they're my favorite). Did I mention that they're seriously comfortable? Whether you need a casual shoe for everyday wear or a dressier shoe for a special event, these shoes should be your go-to."

Meghan Adams, Digital Creator


(Image credit: @imgoodlikelikemeghan)

"I brought these Sperry shoes along for my European vacation this year, and I couldn't be happier. After getting married in Tulum, my husband and I never took a honeymoon, so we're counting this trip as one! Sperry's boat shoes are not only comfortable but also practical, making them the perfect choice for this trip. They're versatile and can be worn with a wide range of outfits whether you're out for a stroll on the beach or dining out in the evening."

Taryn Cumbo, Content Creator


(Image credit: @taryncumbo)

"Summer 2023 is all about being adventurous, and Sperry is the epitome of adventure while staying comfortable and looking cute at the same time. What could be better? You could say I'm a bit obsessed with the brand. I've worn the shoes all my life, and they truly never go out of style. This year, I'll be styling my Sperry shoes with high socks—I think the look is so cute and adds an extra layer of comfortability, making them the perfect addition to my summer vacation wardrobe."

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Anneliese Henderson
Senior Editor, Branded Content

Anneliese Henderson is a Los Angeles–based senior editor on the branded content team at Who What Wear where she covers the latest in fashion, beauty, and lifestyle. When she’s not writing about her favorite trends, you can find her reading a book by the beach or spending money on overpriced smoothies at Erewhon.