How I Got Over My Fear Of Wearing Flip-Flops

Photo: Christian Vierig/Getty Images.
Photo: Christian Vierig/Getty Images.
Earlier this summer, Anna Wintour said that she “loves” flip flops. If we’re to believe her, it says a lot about style in 2019. The zeitgeist dictates that the uglier the trend is, the better. Everything from dad shoes and mom jeans to upside-down skirts is de rigueur, as long as you feature it in a well-lit Instagram photo. This summer, that short list has included flip flops.
Living in New York City makes wearing flip flops a challenge. Walking around barefoot leads to unfortunate encounters with murky puddles on the street. Ask anyone who has braved the city sidewalks in flip flops, they’ve likely ended the day with their toes covered in soot.
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As a fashion editor living in NYC, I ruled out the idea of ever wearing those casual, extremely open-toe flats. So, imagine my surprise this summer to see them creep up all around me. In Soho, I spotted stylish girls pairing them with colorful A-line skirts, t-shirts, and chunky jewelry. Instagram influencers like Emili Sindlev are topping off their brunch looks with colorful plastic sandals. Jennifer Lopez is styling her Givenchy sweatsuit with glitter thong flats. Street style stars at Copenhagen Fashion Week are teaming prairie dresses with bright flip flops. And Saint Laurent even released a limited edition flip flop in collaboration with Havaianas.
Despite the proliferation of the flip flop, I was still skeptical about whether I should embrace the once-shunned sandal. For starters, I never felt that my feet were my greatest asset. I played soccer throughout high school, and I have the callouses to show for it. For that reason, I’m a year-round boots wearer, and it takes a really special sandal to encourage me to let my feet loose. On top of that, as a fashion editor, I feel pressure to pile into vertiginous heels to “look the part.” In the circles I run in for work, the dress code calls for high-fashion clothing items paired with sky-high stilettos. A casual flip-flop — and the comfort it provides — never fit into the arbitrary wardrobe standards I set for myself.
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Hawaii life complete with lei making and flip flops.

A post shared by Alyssa Hardy (@stopalyssatime) on

And then I went to Hawaii for the first time, and everything changed. There, on the island of Oahu, I learned that flip-flops are literally a way of life. Everywhere you turn, you’ll find someone wearing a worn-in pair that locals lovingly call their “slippers.” They don’t limit the sandals to low-key, low-stakes affairs; they pair them with everything from a string bikini to a festive, going-out ensemble. There’s an ease and simplicity to Hawaii dressing that I found inspiring. For a few days, my anxiety over what to wear dissipated and comfort took precedence. And dare I say it: my flip flops were actually cute. My gold platform $20 Havaianas looked, in fact, quite stylish paired with my Alexa Chung maxi dress. And heading out for a coffee, I didn’t have to think too much about my outfit. I could just throw it on and go. I could focus on living.
This experience, coupled with a healthy dose of clear blue water and natural vitamin D, reminded me that summer dressing should be easy. While you won’t catch me on the subway in a pair of flip flops anytime soon because my fear of getting stepped on still persists, I’ve overcome my insecurity about my feet and will now show them as I see fit. Maybe that means wearing them with a t-shirt and shorts at the Rockaway Beach boardwalk with my friends. Or even showing up to a fancy brunch downtown in flip flops paired with my favorite Ganni dress. Either way, my pedicure is finally getting some shine.
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