Some guy at my gym looked down at my feet without me asking while I was mid stretch one day and said “your heel’s hanging off the back of that thing, man.” I hadn’t asked. I wasn’t even thinking about my goddamn flip flops, I was thinking about if I had it in me for one more set. But he said it like he’d been waiting decades to make that exact stranger comparison, and I stood there annoyed because he was right. Mile HIGH. About an inch of my heel just hanging out there in the open air, scraping every fucking step it took just out far enough away that it was auditioning for new problems.
It stuck with me longer than it probably should have. Mostly because I realized after he said it how many dudes are out there walking around in flip flops that are literally sized like an afterthought.
Too small like your favorite shirt after you’ve gained ten pounds, not too small. Tight. Where they still sorta fit and looked fine when you tried them on in the store but become very obviously too small three blocks into a walk because your heel has been pounding concrete for the last half hour. Flip flop fit is one of the laziest fractions of mens shoe sizing decisions there is and I did it too for about ten years of my life.
The fit you need on day one: Why That Overhang Isn’t OPTIONAL
The thing nobody tells you when you’re wearing flip flops in the try on portion of the store for eleven seconds before deciding they feel okay is your entire foot needs to sit flush on the sole. None of it should be hanging off the front or back. Not “a little bit.” Not “half of my foot could go farther but it’s fine.” All of it needs to be completely on the sole of the flip flop. Fit wise, a quarter inch of open room on either side of your foot is the sweet spot, not too tight and not over hanging, it’s where your shoe actually should sit. The majority of guys buy the opposite of this though. They buy them up too tight against their feet on purpose because that’s the only logical sizing method they’ve ever used on shoes and it is entirely the wrong one here.
The heel is the biggest issue by far. If your heel even slightly overhangs the back of your flip flop it’s catching on pavement with every single step you take which not only wears down the sole unevenly and will drive you crazy later, it also means the sandal is stabilizing your step in a way it wasn’t made to. Every sandal is bending at the base of your heel where there’s no mold to account for that type of pressure. I once had a pair in college that I wore to Florida and back because my heel was overhanging the stupid thing the whole week and came back looking like it had been tattooed across the back of a truck. It hadn’t, I just walked around Disneyworld in them. That’s all it took.
Toes are important too but for a less destructive reason. Over hang on the front looks terrible much quicker than it actually starts to negatively affect your walking. It’s not quite as instant wearing down of material as the heel is but if your toes are dangling off the front you are one deliberately placed sidewalk crack away from stubbing your toe because you couldn’t longer clear that same corner you did two sizes too big four blocks ago. Not to mention it just looks like you shrank in the wash when you bought them that small on purpose to save eight bucks because they were on sale. I see it happen all the time actually. Dudes will size down because “the bigger one doesn’t fit” and just deal with it riding past they’re foot like it’s a feature instead of the giant mistake it is. It is not okay.
I get wanting them tight though. Feels like your foot will fly out otherwise, which might happen if you run, but flip flops don’t have straps or shoelaces to keep your foot stabilized while walking, so it feels like it should be tight to compensate. But the entire point of wearing a flip flop is your foot sits on top of a solid foundation versus being wrapped by one. Little room isn’t sliding around here, its what correct flip flop sizing is. Treating your flip flop like a running shoe is by far the most common mistake I see.
The fit you need after twenty wears, because Day One Lies To You
Flip flops lie about how they fit you on day one though. They know foam doesn’t stay shaped forever so what fits on day one will never be exactly how it fits on wear twenty. Every pair of flip flops breaks in after you wear them a few dozen times even if they’re really high quality sandals, and that footbed molding to your foot changes the shape of the space your foot sits in slightly.
With enough wears that “perfectly snug” fit you felt at the store is suddenly too big around the foot because your unique weight and stride stretched the foam unevenly, and there’s literally nothing you can do about that except start over with a new pair. That “just bought them today they feel great!” fit starts slipping around after a certain point because every pair stretches slightly where yours are sliding forward because the tight spot under your arch has stretched with wear.
I have a pair right now that’s done exactly that. They’re 4 months old and the front post that holds your toe in place has stretched just enough that I catch my toes slipping forward on stairs and have to constrict my own toes just to walk normally again. Is that what you consider “worth it” to your 50 bucks? I feel like I did when that happens. That’s not a defective product that needs to be returned. That’s what foam and rubber is supposed to do after repeated wear, however annoying the consequences might be. It means that while you do need them to be snug on day one, you also need to mentally account for them getting looser with time when you buy them because sandals are the only shoes people will willingly wear for 2 straight years.
The dudes that do this buy almost embarrassingly snug on day one because they know that no matter how well you think you fit into that day one box it’s going to get looser, and then they’re okay with that sandal getting just a hair bigger around the foot over time. Nobody tells you that little piece of info because “adjust for stretching” isn’t an easy thing to print on a size tag, it’s an “I’ve destroyed eleven pairs of sandals trusting them to not stretch” type of deal.
Trust me, I counted, my drawer is full. The ones that still fit great at wear fifty were the ones I remembered as being snug in the store. The ones that became a gnarled, slipping mess by summer were the ones I remember thinking “jeez those feel nice, barely gotta wiggle them on” when I bought them. Worst feeling is when you look back and realize it didn’t fit right day one, it just fit early.
So how do you actually wear flip flops? Both of the above. Buy them with where they’ll end up after six months of Sundays in mind as well as how they fit the moment you try them on. Fit them to your foot now, allowing that ever important quarter inch on either side and no excess over hang anywhere, but buy knowing they will get looser from there. Because they will and when they do you’ll either be good to go all summer or you’ll have this conversation with yourself again about how you SHOULD have known better than to let your heel hang off the back like a fucking spoon.
Marcus started the menswear section after getting fed up with coverage that called a two hundred and fifty pound hoodie an easy Tuesday buy. Based in London, he writes about pricing, returns policies and what brands actually deliver.
