Do You Hate Heeled Flip Flops?

I rarely feel lukewarm about anything. Even if I don’t have a fervent opinion…an opinion, I always have.

Heeled flip flops are a shoe that don’t bring much up in me. I don’t love them and I don’t hate them. Sometimes I consider getting a pair, but then I don’t.

The only reason I can conjure to explain why I have not purchased a pair is because my gay straight bestie hates them. He doesn’t just hate them, because he hates a lot of things, but he HATeeees them. He cannot seem to really explain why…but, he feels passionately about them. I’ve noticed a lot of men feel this way. And you have to respect their freedom to opine.

I don’t exclusively dress for the male gaze but, when I don’t it’s for a fashion item I could not imagine my life without. So when I’m humming and hawing over heeled flip flops, all I can hear is my gay straight bestie telling me they’re so ugly and I decide, I do not need them. I trust his opinion so, I have been waiting to see if his hatred for the heeled flip flops will infiltrate my brain and allow me to finally see what he sees or, alternatively, whether I will develop a strong need for them. Neither have happened yet, so I’m writing this.

And the only reason I can think of to explain why men hate heeled flip flops so much, is that you look stupid when you walk in them. And it’s true. The click-clacking around of a regular flip flop is bad enough. The noise of a heeled flip flop is even worse. They are wood and leather instead of plastic/foam so the clacking is loud and grating. Especially when you are running or speed-walking. And especially when you are missing the heel caps.

It’s possible that men also just see them as a flip flop, with a heel; instead of what they are, which is a heeled flip flop. They are not perceiving this shoe as an independent item: a heeled sandal.

Women and fashion lovers might understand this idea through the concept of a sneaker with a heel (I am thinking of those ugly Miu Miu sneakr heels). A ridiculous add-on to a shoe that is commonly worn in it’s original variation and is extremely popular. We can also call to mind the New Balance sneaker loafer. Same idea. We know it’s a sneaker, but we’ve added a loafer bit.

Heeled flip flops are not that. They are a shoe in their own right.

Men are seeing HFF (heeled flip flops) as another shoe we girl-ified. So I do sort of understand. Why they might think it looks silly. But that, according to me, is misogynistic. (I am very into calling out misogyny as it regards to making women feel silly for being girls, being a girl is amazing and we should never feel frivolous or trivial for it.) Because why can’t we girl-ify a shoe? Let us live. Being a girl is not silly. We need to stop this.

The HFF rose to popularity maybe two summers ago? During the summer of the capri. Which was also the summer of the flip flop. Flip flops continue to rise in popularity as evidenced by all the ongoing Havaianas and Brazil fever. We are no doubt going to experience unchartered levels of Havaianas collabs this summer.

Flip flops were obviously made cool by the Olsen twins. What about them exactly, is so chic? I realized today—while trotting in my new Carhartt Brandon pants, Walmart boys section camouflage tee, Repetto black patent Mary-Janes, and my Aquascutum trench coat generously gifted to me by my bestie, Alexe, and which I receive so many compliments and comments on and it truly, fits me like a glove—that contrast is a definitive pillar of my #aesthetic.

The middle of my outfit makes sense, a camo tee with workwear pants. The extremities of my outfit also make sense: a trench coat + little ballerinas. The HMUA is also somewhere in between, my hair parted in the middle and straighter than usual but, makeup very dewy with an nearly red lip. This is known as the sandwich method. And what it says essentially, is that you cannot tell what kind of girl I am. I am girly but, not exactly. I am boyish but, not exactly. I am unpredictable. Simply irresistible.

I am getting into pick me territory here. And so what if I am a pick me, by the way? I think I might be. Anyway this is by no means a revolutionary idea but, I think contrast just is what makes anything interesting. Combining things that aren’t supposed to go together but, make sense anyway. This is why girls love wearing ballerina flats with basketball shorts and a little frilly top. Is she sporty or is she girly? Why not both. She is layered and complex. You cannot put her in a box. Please recall my note on misogyny from earlier. I think this type of thinking is sort of in retaliation to that. Do not force women to choose.

But that’s what makes flip flops feel interesting. You are almost wondering why people like the Olsen twins would wear them. To put it dramatically, it adds depth to someone’s character. When they could wear any type of shoe, why choose a flip flop?

I did some research…

Did you know that we call them flip flops because of the sound they make? Originally, they were widely known as thongs. I hate when people call them thongs. Not because it recalls the undies but just because it feels like they want to be provocative for no reason or European when they are not. I can hear the difference btw when someone calls them thongs authentically and when they’re doing it performatively.

They were considered cheap and informal for a long time. Think of the classic American dad on vacation who refuses to wear anything other than shorts, flip flops and a hawaiian shirt to dinner. Grounds to send him home. Not meeting the door policy. It’s kind of crazy to picture that type of straight man in flip flops because well, as we all know, it’s disgusting for men to have their feet out. But, nevertheless, it happens. And there’s a reason why there are signs prohibiting flip flops in nice establishments.

Last summer I wore my black Havaianas almost everywhere, at every occasion, and as early in the summer as I possibly could. Aside from the impeccable vibe they bring, they really do go with every outfit.

They also bring a welcome solution to my age old issue of pants dragging on the floor. If you size up in your flip flop then you have a little extra room in the back for your baggy pant to rest on. A little shelf. And that is extremely important to me. That is why I love my great great great ex bfs size 10 Nike slides. If you’ve been to my house you’ve seen me wear them. Ridiculous to think that when I worked at SSENSE in 2019 I wore those to the office.

Ok so back to the last summer.. since moving to Montreal and befriending Alexe I have adopted a sort of New York way of dressing. Leaving the house in an outfit that I could feasibly wear all day to a lot of different types of events. So whether you see me at 11AM or 11PM my outfit suits the vibes. Mostly.

That makes a flip flop very useful actually. Because if the rest of your outfit is chic, then the flip flop can take you pretty much everywhere.

I met a wacky dude at a bar who asked me if I could only wear one shoe for the rest of my life what would they be and without hesitation I said flip flops. I also don’t want to live anywhere where a flip flop wouldn’t be appropriate footwear year round.

Butttt, having said that, there were nights when I went out in the flip flop and I did feel a bit embarrassed. Wishing my feet were not out. Wishing I could have had a chance to WASH them because they were probably filthy. Fearing that someone would step on them. I felt exposed and informal in a way that I did not love.

Ultimately of course it was fine, it was just interesting to observe that feeling. Where I felt like flip flops could do no wrong because I have been The Row brainwashed to believe they are classically chic but, a deep part of me knows they are a casual shoe that actually used to be considered unfashionable.

When you love clothes and you see them presented a certain way, sometimes it feels like they always existed like that. It is so natural to see the Olsen Twins in flip flops that it becomes hard to grasp that they did subvert the longstanding perception.

I forgot that 20 years ago baby Picky (me) was judging families on vacation in hawaiian shirts, shorts, and flip flops. Thinking ew they’re so gross. Get real shoes. But, flip flops are real shoes. They’re elite shoes. And actually today, I’ve understood that nothing is off limits. Nothing is ever a categorical no.

For example, I was trying to find photos of Carrie wearing HFF but I could not locate. She wears a lot of heeled sandals, which, spiritually don’t feel any different to me as I already said but, in my search I ended up on a reddit thread talking about the contradictions in what Carrie said she’d never wear (a scrunchie and furry shoes) and evidence that she did in fact wear those things:

So now girls are wearing HFF.

I find it shocking for these shoes to be so contentious because they are really just a heeled sandal. Like it’s really not a big deal or any different from any other heeled sandal.

So I still don’t know how I feel about a heeled flip flop except that maybe, I don’t see the big deal? They’re just heels like any other. But I guess I would prefer a regular heeled sandal over a heeled flip flop.

Like these Christen heels which, apparently are very uncomfortable but so chic and WHITE which I have been after, are so beautiful.

They remind me of my Signum heels from The Row which my gay straight bestie also hates but which I love and don’t consider to be flip flop. Though sometimes I do feel like they look like ankle cuffs or restraints.

And if I want to wear a flip flop then why wouldn’t I just wear a flip flop? I did just purchase these Zara Christopher Esber knockoffs that I am very excited about. ANd I think I’d rather rock those than HFF…

We could get into the weeds of what makes a good heeled flip flop and what makes a tacky one. Because of course I have not yet touched on all the nuance.

The wedge is cute IMO if it’s conservatively low:

I love the jelly shoe clearly and I like the heel height here and the way that it comes from the middle of the heel and not straight down the back of the edge:

Here we have two pairs of heels from Jude and as you can see, the heeled option that is just a regular sandal is so much more chic and elegant:

Though I guess the flip flop is more city girl Calvin Klein 1990s SATC vibe. I don’t really love the triangle shaped heel:

These I love, though they are a bit high. I love the silhouette of the front sole, it’s perfect elongated and slender and rounded but not too round. I love this shape. I love when it tapers in a way that resembles the anatomy of the foot. Just perfec.t

These, horrible and ugly. Hate the square stiletto it’s fugly. Hate the square toe. Hate square shoes in general. Straight gay bestie agrees but actually I know this because we disagreed over a pair of square shoes I wanted. I don’t remember what they were now. But, these look cheap. I can’t even start on the flip flop portion which just looks cheaply done and is bulky and clunky. I also don’t know what’s going on with the sole but, something is wrong there. You can j ust tell these will be uncomfortable.

These are more well-made, but they are also ugly. It’s the square toe. It’s how thick the straps are. It’s the shape of the straps, how long they are like they go too far back on her foot, she is too strapped in. I don’t like how chunky the heel is AND that it kicks inward. Just no.

These Manolos, sey as hell. Thin straps, very chic and simple and clean. Little heel. Slip sole and again perfect silhouette at the front, kind of curved and tapered off. I love. These are the perfect like barely there shoe where its just like they go with everything and feel like a naked shoe.

These Toteme are ok. I wouldn’t pay for them though.

Same with these like idk what brand this is but, they are chic-er than some of the earlier options but, ya idk I’m looking at them and I’m just like do I need these? Not sure.

So maybe in conclusion, I agree with my straight gay bestie. Just wear regular flops.