We Investigate: Can Flip Flops Be Cool?

Not a trick question


I have recently rediscovered flip flops. This probably sounds every bit as curious as it is, namely because it seems unlikely that one should have to rediscover such a ubiquitous style of shoe. But I ask you to consider the following question: when’s the last time you wore your flip flops as an intentional style choice? That is, to add pepper to the dish that is your outfit? An unlikely but much welcome punctuation point to the end of your sentence? I can go on but these metaphors tend to stop making sense around the third try and you have probably drifted into the vast and nostalgic world of early 2000’s paparazzi shots of O.C. actors and the like… Am I right?

Paris Hilton (by Lester Cohen/WireImage via Getty Images)

But who’s responsible, really, for this recent interest in “taking back” flip flops?

My guess is Fashion.

Louis Vuitton and Dior started seeding the idea of thong-style rubber sandals worn with ready-to-wear for their respective Resort 2016 collections last May. When I first saw them, I guffawed. Then I wrote about them while I was guffawing. Then, when Hedi Slimane’s Saint Laurent put out a pair with a rainbow sole and asked for $475 for them in February, I near lost my shit, and wrote about that, too.

But here I am. Understanding both the acute manipulative power of high fashion but also that I might still be letting loose. When I set out to get dressed this morning and surmised that I would wear flip flops, I felt indelibly liberated. Like I was free from trends, that no one could say anything about me I wouldn’t say myself. When I look down, I feel curiously empowered by the lack of statement I’m making through this statement and so if you’d like to try it for yourself, here’s what you should know. (Other than, I suppose, that it is so clearly August and the fashion cycle is so clearly on hold, I am seriously intellectualizing a pair of flip flops.)


1. Don’t Overthink It. When styling your flip flops, forget athleisure and normcore and all the cues that have defined the fashions of recent years and instead focus on your classics. Have a favorite pair of jeans? And a button down shirt? Great! They will look so neat with your flip flops. Here’s also a great place to explore your ACCESSORY BOUNDARIES. That is, how far can you take your limbs before you’re actually strength training while you type?


2. Do Clean Your Toes. I’m not a particularly large fan of painted toenails unless they are done the French way but do appreciate a clean set of toes just as much as the next nail technician. If you’ve been meaning to get a pedicure but have been putting it off because, whatever, now’s your chance to marvel in the glory of a foot rub and heel scrape. Go for it.

3. Ask Not What Your Flops Can Do For You, But What You Can Do For Them. I’m still not completely sure what this one means. Get back to me in twenty.

4. If You’ve Spent All Summer in Blisters, Congratulations! You’re Relieved. This one is pretty self-explanatory but basically you’re wearing sneakers, only you’re entirely exposed from the ankle down. Run a marathon if you want. Yolo.

Photographed by Krista Anna Lewis; slideshow via Getty Images and Vogue Runway.


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  • Natali

    Well, anything that you wear is the coolest combo ever, so yes, flip flops can be super cool and they’re so comfy too, so it’s a win-win situation. 😀


  • Senka

    Not sure about flip flops unless I’m at the beach which I’m still very much not, but damn those jeans are cool. And that basket.
    You make the flip flops look french, not exactly sure how, but you do.

  • Last year I walked six miles on Manhattan island from Inwood to the upper east side (this was only a warm up for my long day of walking. Who knew NY had so many hills…). At the end of my trip I found myself staring at a pair of flip flops. “AAAAIIIIRRRR AAAAIIIIRRRR” my feet gasped. “Shut up!” I snapped. All throughout high school flip flops were THE shoe, even in the winter. (I’m from Maryland…) When I left that world to go school in Chicago, I vowed for my toes would never be that close (or open) to the ground again. Although I did not buy those flip flops that fateful day, I have been thinking about them ever since. The next time my feet beg for the sweet sweet relief of a thong, Ima let em have it.

    Plus they kiiiinda almost go with everything (????) and they make you look super chillax.

  • Katrina Lee

    I want to get in on this because ugh, tying shoelaces, am I right? But too long a walk in flip flops and my knees and hips hurt. I guess the need for support is real.

  • The Fashion Mixologist

    Love your blog. It’s hilarious, and flip flops sound like an excellent idea actually 🙂

  • Sofia Allyn

    Where is your amazing basket bag from though?!

  • Funny, I may or may not own 2 pairs but have decided against wearing them because everyone around me seems to. Will be doing sandals instead – and checking out how far blue toenails will get me …

  • Alyssa G

    I’m still a little iffy on flip flops. I’m moving to college in two weeks, so as of now, I just think of them as shower shoes. The only ones that I think I’d be comfortable wearing as part of an “outfit” are Rainbow flip flops, since they at least look a little better than the classic foam/plastic ones.

  • Ryan

    Ok but on another note LEANDRA WHERE ARE YOUR JEANS FROM

  • Stephanie

    In Indonesia almost all of the people here loves wearing flip flop! The very famous brand from Indonesia that maybe you can find on e-bay is Swallow.



    I decided to go barefooted at home about ten years ago when I got seriously into yoga etc, and it suits me fine. There was a similar flip-flop trend rewinding five years ago but I don’t follow it. Now flipflops come in all kinds of patterns, but I couldn’t care less. At home my feet have liberty. I tried to run barefooted while running a half marathon, cos I’ve seen people do it, But I guess you need practice. I had the genius idea to do this halfway through because my trackshoes were hot. Bad idea. The concrete felt like well…concrete…under my soles. I can still recall my arches curl up in dismay. And it was nearly noon, so the ground felt like a furnace. I am an idiot.

  • MT

    Kino Sandals. https://kinosandals.com/adult-sandals.html

    The classic Lily cut in black leather is the solution to all of your “but flip flops are actually hideous” woes. Or any color leather. Or any of the other cuts, honestly, but I fucking love them. Hand made in Key West by people who seriously know what the fuck they’re doing. A+ highly recommend.

    • Gene

      They’re lovely. Keeping them in mind for next year!

  • Ellie

    I feel like backless loafers are my new flip flops.. Freedom of the feet, flips and flops, the inability to walk at a fast pace but no toe stubbing!

  • just_parsley

    I’d like to be a few inches taller so I’ll take a pair of those 5-inch high elevator flip flops* if you please. 🙂

    (*Picture 13, “Marni Spring/Summer ’14”)

  • Paula

    For Australians, flip flops or thongs as we call them, are the national shoe, all year round. I hate it, because really, there’s a time and a place for them. I’m living in Canada at the moment, and it’s great to see people wearing proper shoes in summer.

  • Paula

    PS. The funniest wearing of thongs I’ve seen was at Whistler in April. A ski patrol chap was wearing thongs with his ski gear, sitting on a skimobile, on the mountain.

  • Nina Marini

    Hi Leandra,

    I’m a huge fan of your site and I remember following it back in the old days – when it was truly man repelling 🙂

    You’ve inspired me to open up my own blog, http://www.honestfables.com. It’s just a compilation of my creative thoughts and stories. Hopefully it’ll be as successful as yours one day.

  • I am from China. My dad HATES it when I wear flip-flops. He thinks wearing flip-flops in public is not a proper thing to do…disrespectful to others.

  • Beatrice

    So very Rio of you!!! My mom always trashed flip flops but I also grew up basically in a pool so…. I love them. 2000s were a dark time to come of age because plastic shoes are now nostalgic

  • Lo

    flip flops make me harken back to showering, always showering, at summer camp or college — most recently i tracked down a certain pair of black, slim havaianas from a brazilian ebay seller that have the strap closer to the toe, as opposed to greedily reaching back to the middle sides of the foot. this somehow felt more refined, different, yet at the end of the day i was still wearing a flip flop. at the ripe old age of 27, my feet (not me) nearly demand at least a bit of arch support…henceforth, now and forever, I’m afraid my flip flops will remain a to-and-from shoe based on practicality or lack thereof, only to grace the floors of yoga, spin, and pilates studios. i think they are probably the most hygenic option if they’re rubber, because of ability to wash so…yolo

  • Katie

    I’m born and raised in Southern California where people literally wear flip flops year round. I prefer to just wear them to the beach or pool, but there’s kind of a cool, I don’t care attitude about throwing them on with something more put together.

  • Aliin

    1) Lol, i always feel a tad bogan when i wear my thongs outside of a beach/ pool context.
    2) What brand is that shirt? I’m a recent blue shirt > white shirt addict.

  • Rebecca

    So I have major joint problems that cause me excruciating pain, basically all the time. Especially when walking. Flip flops are out (the summer ritual of buying a new pair from Accessorize (UK ladies, you’ll get me) is forever gone alas), elegant sandals with slivers of leather between me and the pavement are out, but ALSO birks etc are out, because without any ankle support my rubbery joints bend and I a) fall over and b) break ankles. I hate summer, especially the heat, but have NO CLUE what footwear to go for so I can still a) look cute and b) not melt.

    I’m aware I’m hunting for a pillowy-soled elegant unicorn here, but I have to try! I’m determined not to let this stupid, infuriating, heartbreaking thing ruin my sartorial existence as well as my general day to day life, but I’m telling you, orthopaedic shoes are giving it a good go…

  • Georgia

    Yes. But also thongs never went out of fashion in Australia.

  • Love this, I’m in Bali at the moment and reintroducing myself to the foot thong.

  • Mariana

    Flip flops (specifically Havaianas brazilian brand), are a big think in portuguese summer. I personally love it, my feet seek freedom this time of year.

  • One word: this is me in August, 2014 acting cool by titling an outfit post “Jeeen over Jeeen” (WHAT???) http://www.fashionparadoxes.com/2014/08/02/jeeen-over-jeeen/, noticing that I evolved as a person/ title creator, but never as a flip flops wearer, I can wear THIS today and call it a perfect relieving day.
    No, I take that back, slides makes me feel that now.

  • In Australia flip flops are such a staple they sell them in vending machines.

  • doublecurl

    I cannot tell you how validated I feel that the ONE pair of flip flops I own are those worn by Leandra here

  • This is so interesting to me because ~as an Australian~ flip flops (or rather THONGS lol no shame) are the most natural thing in the world and – take it from a native – they honestly go with 85% of your wardrobe. Don’t fight it!

  • Mary

    I think Rainbows + skinny, skinny jeans that go all the way (not ankle, yaknowadimeen) look really, really cool. But only Rainbows, and only the OG ones – they’re our ~*~aUtHeNtIc~*~ San Diegan normcore contribution.

    • Lou Gomez

      not a good look

  • Megan

    “I saw Leandra Medine wearing army pants and flip flops.. so I bought army pants and flip flops.”

  • Lou Gomez

    I live in Florida. People wear flip flops in December and January, even when it is 40 degrees. Gross. Show some class.