Anna Wintour approves of flip-flops, yet does not approve of ‘casual’ looks

Anna Wintour

I would love to know what committee and/or pollster was tasked with telling Anna Wintour that she needs to be more relatable. Anna Wintour exists in the zeitgeist as Nuclear Wintour, the woman with a face like thunder, who will never approve of your ensemble, your purse, your shoes, your makeup, your hair or your face. Anna Wintour exists to judge, and she will always find the rest of us wanting. But over the years, I feel like *someone* at Conde Nast has been like “at least have a little fun with that image.” Thus, she does stuff like weird little cameos in Ocean’s Eight, and now Vogue has an ongoing video series “Go Ask Anna,” where Anna answers questions from people on the street as she sits in her impeccable Vogue office in the middle of the day wearing dark wrap-around sunglasses.

The current episode of Go Ask Anna is a good one – she covers a lot of topics, from Rihanna’s new collection (Anna likes that Rihanna’s not going for trendy), her favorite shoe (Manolo Blahnik), her admiration for Serena Williams and Jacinda Ardern, her wardrobe full of print dresses, and how she’s not a big fan of “casual” looks. She says, “Personally, I’m not too big a fan of ‘casual.’ I prefer when someone errs on the side of ‘dressed.’ There was a member of our team who turned up at the Met Gala recently without a tie and wearing a hat, and I’m not sure that I approved.” But then she’s asked about whether flip-flops are acceptable outside of a pedicure and Anna SHOCKED me by saying: “I love a flip-flop!”

I can’t believe it! All these years, people mocked my flip-flops and here’s Anna Wintour giving me the thumbs up. Seriously, I love flip-flops and I would wear them year-round if I could. I wear them for comfort and I have so many that I can totally coordinate them with my outfit if I so desire, but I never dreamt of getting Anna’s approval. Now I have it and I feel so fashion-forward. Anna Wintour truly is a woman of the flip-flop-clad people!

Anna Wintour arrives at the 2019 CFDA Fashion Awards held at the Brooklyn Museum on June 3, 2019 in Brooklyn, New York City, New York, United States. (Photo by Image Press Agency)

Photos courtesy of Avalon Red.

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65 Responses to “Anna Wintour approves of flip-flops, yet does not approve of ‘casual’ looks”

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  1. BengalCat😻 says:

    Who gives a shit what this out of touch, Kardashian loving Gremlin with 1985 hair thinks of anything. American Vogue is a terrible magazine. She needs to go.

    • NicoleK says:

      My thoughts, straight out of your mouth!

    • Tanguerita says:

      this, this and this.

    • Harryg says:

      Thank you!

    • Chica71 says:

      She wears same shoes with each outfit. Beige Manolo sandals .. I guess she goes for comfort

    • minx says:

      Just what I was going to say. Putting a Kardashian on the cover of Vogue? I don’t care what she has to say.

    • AppleTartin says:

      easy on the bob shaming @bengalcat – they are timeless, classic and easy to maintain. I have thick hair and it’s the only style that works for my face and hair texture.

      • BengalCat😻 says:

        I don’t mean to bob shame. I meant that I don’t think a woman who’s had the same hairstyle since the early 80s should be making judgments about fashion. I would love to be able to rock a bob but my hair is too thin and stringy. No offense intended ❤

      • jennifer says:

        i have a long bob, but bob shaming? really?

  2. Valiantly Varnished says:

    Anna is wrong. Sorry. Flip-flops are the worst things ever invented to be worn. The ruin every look. They are worse for your feet than heels (an orthopedist told me this!) and they are just plain UGLY. I call dudes in flip-flops “lady boner killers”.

    • Lee says:

      This is very true. I don’t wear them anymore, because I once had a tendinitis because of them! It was painful!

    • Becks1 says:

      I wear flip flops to the pool and that’s basically it. I have bad feet anyway (bilateral plantar fasciitis) but my right foot also has two bone spurs in my big toe, that make flip flops very uncomfortable (because of the way your foot needs to grip it as you walk.) So while I don’t dislike them, I cant really wear them.

    • Seraphina says:

      I so agree. I hate flip flops. Flip flops are for the beach, pool or shower. I also wear in a motel room so my feet don’t touch the rug or bathroom floor (yeah I have issues).

      And men in flip-flops are a lady boner killer (which is hilarious). There are so many shoes one can wear instead. And they offer no support. Never got the infatuation with them. Plus, they hurt my toe :(

    • Snazzy says:

      I hate flip flops so much. Thank you for sharing this hatred with me

    • Otaku fairy... says:

      I don’t like flip flops either. They’re uncomfortable – it feels almost like you’re not even wearing shoes, and depending on where you wear them you feel dirt on your feet.

  3. Charlie says:

    I read Anna Approves of FlipFlops and thought “Anna approves of Kardashians”. Done.

  4. Maria says:

    She’s been washed up for years. The magazine has gotten so horrible nowadays. It’s time for her to go.

    • PointingScreaming says:

      when looking at vogue, I realized I was paying for chemical smells (perfumes? blahhcchh) interspersed w air brushed anorexics in 10K dry clean only get ups. My fashion is vintage wearable hand washable, with actually comfortable shoes. Anna has to be carried up and down stairs due to her manolo love. WTF?? I haven’t bought or looked at a vogue since I was a seriously stupid ‘tween.

  5. KidV says:

    Depends on what type of flip flop you’re talking about. The thin, $2 ones you wear to the pool, that’s a no from me. But there are so many cute styles of flip flop out there now. I wear them all year.

  6. Lory says:

    I’m in no way a fashionista and Wintour would very much side eye my ensembles but I agree with the “dressed” part. No need to wear a ball gown everywhere you go but I’m sometimes shocked by what some people wear to professional and/or formal situations.

    • Moneypenny says:

      Me too. In my mind, it is always better to be overdressed than underdressed. I hate how casual people can be at work!

      • FoundCat says:

        I was born overdressed and don’t look American. My soul deeply loves fashion & creativity & abhor box store apparel. Still I can’t abide the dead eyed skinny models of today. I won’t support Vogue style misogyny.

  7. sassbr says:

    What’s with the hate for the flip flop? I love a flip-flop, like a nice plain leather one or jewel tone. They’re just a nice flat shoe for going to the store real quick or walking around the house or on vacation, especially if you have nice feet or ankles. I used to love Jennifer Aniston’s casual look-the tank top, cargo capris, with flip flops. She always looked so good. I’ll rock that look for a barbecue or casual patio drink any time.

    • smcollins says:

      No hate from me! I LOVE my flip flops, and outside of work they’re my go-to spring/summer footwear. I also live close to the beach, so there’s that, but even if I didn’t I’d still wear the hell out of them!

  8. ew says:

    I would love for her to properly live outside of her NY/London/Paris bubble and be shocked by how 98% of the world don’t care about her opinions. She’s so ignorant.

    • olive says:

      i don’t think she’d be shocked. i don’t think SHE cares enough about those flyover areas enough to be bothered by them not caring about her opinions. she said people in my state look like “little houses.” i don’t think she cares about the opinions of “little houses” – her opinions matter to the people that matter to her.

  9. Hanahk says:

    Have broken my toes twice while on vacation wearing flip flops, once fell down a ditch in Costa Rica wearing them as well. They are dangerous be careful!!!

    • MaryContrary says:

      I sprained my ankle wearing them. I only wear them for the beach or the pool. And I live in SoCal, land of the flip flop/yoga leggings/sleeveless shirt/trucker hat.

  10. Fluffy Princess says:

    I love a flip flop too. I live in LA where it’s usually sunny and warm all year round, so it’s a flip flop fandango out here. . .

  11. olive says:

    flip flops are disgusting, i don’t want to see your dirty feet and toes – and they ARE dirty, because you’re wearing flip flops and your feet are completely exposed to the elements!

    • KidV says:

      I’m sure feet are no dirtier than hands, do you expect everyone to wear gloves? And hats? Hair attracts a lot of dirt, like a magnet.

      • Boxy Lady says:

        Since your feet usually are closer to the ground or the dirt than your hands or your hair, your feet probably are dirtier in flip flops than those other body parts.

      • KidV says:

        You’d be surprised at how dirty human hands are. Especially if you have any length of nail.

      • Boxy Lady says:

        I work with money aka “the filthy lucre” all day so not surprised at all lol.
        I’m still sticking to my previous opinion though.

      • KidV says:

        I do get what you’re saying about feet, but they don’t get any dirtier than someone wearing sandals. And I can’t imagine going through the summer not wearing sandals or flip flops.

  12. manda says:

    Flip flops are very bad for your feet, they cause stress on your toes from the gripping and there is no support for your arch or your ankle. That being said, I always liked them too. But only if they aren’t dirty looking (white flip flops make me gag because they are hardly ever actually white anymore) and if the foot inside is also not dirty looking (gag gag gag, dirty feet!) / is pedicured (and I don’t mean painted, I mean not all busted up).

    • Moneypenny says:

      This. They are horrible for your feet. I used to wear them all the time, but then my already messed up feet rebelled. I certainly don’t mind others wearing them…as long as their feet aren’t visibly filthy.

    • KidV says:

      Not all flip/flops. Fit Flops are very supportive, so are Clark’s flip/flops. I wear the hell out of both.

      • manda says:

        Yes, that is true, but I always preferred the bad-for-you ones–that is, the ones with skinny soles and skinny straps. Reefs were always my brand of choice. These days, I pretty much stick to socks and shoes

  13. Boxy Lady says:

    I hardly ever wear flip flops because my foot needs more support. I’m cool with seeing them with shorts but with long pants, no. That is, outside of a pregnancy, injury, or pedicure situation. Otherwise, to me, it’s like, putting on long pants was so strenuous that you now have no energy to tie your shoes. It’s like you just gave up in life.

  14. SM says:

    What is she doing with all those sharp pencils on her table? Nails casually dressed employees to the wall?

  15. BW says:

    I don’t understand how Anna owns all these famous jewels from former royals, including necklaces with huge gems, and then she wears them with print dresses where they completely disappear into a high neckline and are camouflaged by the prints.

    Also, the hairstyle and glasses are designed to hide her wrinkles (or plastic surgery scars) and fool no one. The hairstyle is dated. Her clothing looks dated. I don’t get how she thinks she gets to dictate what’s “in.”

    Maybe she doesn’t truly know what flipflops are? Maybe she’s confusing them with thongs (pun intended)?

    • Bella Bella says:

      I’m convinced that is a wig. It’s very rare for someone her age to have that much hair.

    • himmiefan says:

      I saw the documentary on Vogue’s September issue, and Anna struck me as someone who feels like a fraud. I think she has immense talent, but she also seems intimidated by Grace Coddington.

      Anyway, I’m so not worried about her opinion.

  16. Spike says:

    I despise flip flops for so many reasons. So yucky.

    I’d rather wear hiking sandals. They are better for my feet, have traction and IMHO are more stable. Some can be pretty cute. I like Keen sandals. They’re pricey but I’ve gotten good deals on eBay.

    • Some chick says:

      Keens are super comfortable if they work with your foot shape.

      I live in a gritty city, so sandals aren’t generally my first choice. I wear socks pretty much year ’round. (Yes, I know, it looks terrible with sandals, which is part of the reason I rarely go for them.) Toe socks can be cute with sandals, tho! Mostly I just don’t want to touch street detritus. (Yes, I have issues too.)

  17. Mego says:

    Her Hair looks like a wig from the Raquel Welch collection.

  18. Tiffany :) says:

    I gauge my foot exposure by where I’ll be walking and how clean it is. City streets can be so gross, and the thought of wearing sandals on them, flip flops or strappy heels, gives me the creeps. But I’m sure I’m being extreme about it.

    • Some chick says:

      This is the comment I should have replied to.

      You are SO NOT being extreme! I’m exactly the same. I want to scrub myself with disinfectant if I wear sandals on the street!

  19. bella says:

    I have seen photos of Anna when she was younger and she used to know how to dress, but now –I say no to the print dresses! It’s ok once in a while, but everyday, and she wears a different dress 365 days a year! I just don’t know what happened. I googled her and lots of pictures of her when she was younger wearing great outfits! I am don’t wear flip flops unless I have to. I totally get why people like them.

  20. tuille says:

    If that isn’t a wig, Anna has the world’s best colorist. I love the very tiny, barely distinguishable gold glints.

  21. Sue Denim says:

    I actually thought she was more thoughtful about fashion and politics than I would have expected, and I love love her necklace. On flip flops — I so love the casual old school freedom but agree they can be bad for your feet — but Olukai’s are amazing! They have really good arch support and cushion, I highly recommend. Used to love Manolo’s but the quality has plummeted in recent years — they use such cheap plastic for the heel tips that my old school, award winning cobbler was shocked, he was like, people could get really hurt slipping w this…and the quality of the leather is also not the same at all…

  22. Mabs A'Mabbin says:

    Personally, I’m not too big a fan of print dresses (can’t stand them really). And flip-flops are an assault on my eyes. I expect to see them at the beach or a pool, but they’re everywhere today. People and their ugly ass feet are everywhere lol.

  23. Rose says:

    I don’t take fashion advice from someone wearing that obvious of a wig.

  24. Flying fish says:

    Why would anyone take fashion advice from her? She used to be attractive but…

  25. Yes Doubtful says:

    Didn’t everyone stop caring what she thought the moment she let the no-taste Kardashian’s and Kanye into the fold?

  26. Patty says:

    Flip flops are okay as long as your feet are clean, moisturized, and you don’t have dirty crusty heels. Most people however, do not follow these guidelines and there’s nothing I hate more than seeing someone’s gnarly feet; especially in places were food is being served.

  27. Alyse says:

    I saw Cady Heron wearing army pants and flip flops. So I bought army pants and flip flops.