Why men in flip-flops seems to be the ultimate fashion red flag

“Men who wear flip-flops in public, run,” Dakota Johnson declared—and honestly, she might have a point.

There’s something deeply unsettling about seeing unpedicured toes peeking out from rubber straps on a crowded pavement. It’s a red flag that doesn’t just wave, it screams. Yet, in 2025, it feels almost cruel to be too harsh. It’s the year of forgiveness, after all—the year we let men experiment a little, loosen up, and maybe, just maybe, embrace their fashion freedom.

Still, flip-flops are a difficult territory. On the right man, with the right outfit (and clean feet, please), they can look effortlessly cool. But for every Jonathan Bailey confidently striding into a London press event in The Row’s designer pair, there are a dozen others giving off “bathroom slipper” energy. The margin between relaxed and reckless is thin—quite literally, like the straps on those rubber Havaianas.

What the girls are saying

I asked some of the girlies what they thought, and here’s what they said, because if we’re going to discuss men’s fashion icks, we might as well get the real talk.

“The thin thong strap ones, yes. Ruined Lucas for me in One Tree Hill season 2, but if they're thicker straps then no.”

“Yes! Unless it’s at the beach or home, I don’t think flip-flops are a great look on a boy.”

“Slides are bad for me. Nice leather chappals can be cute, but only if they fit the event.”

“Nooo, I don’t think it’s an ick—it can be kind of chic if they’re Havaianas and their feet are clean.”

“Why am I wearing makeup and you’re in rubber flip-flops?”

“I get comfort, but wearing them on a date screams ‘I don’t care.’ That’s one of the biggest icks.”

“But for errands with a tote bag, I like it.”

“Their feet are so close to the ground... also, why are you curling your toes for grip?”

The case for chaos

Truthfully, flip-flops are more than a fashion statement—they’re an act of rebellion. They reject structure, conformity, and polish. In a world obsessed with “quiet luxury,” there’s something subversive about a man showing up, toes out, unbothered. Maybe that’s why the look keeps returning, season after season. Whether it’s Matthew McConaughey in 2001 or Beckham in 2004, the message has been the same: freedom first, fashion second.

Yet, that confidence must be earned. A man in flip-flops should know how to balance casual with composure; pair them with tailored linen trousers, maybe a crisp shirt, not gym shorts and a graphic tee. Otherwise, you risk crossing into “errand run at 2 pm” territory instead of “effortless Sunday coffee stroll.”

At the end of the day, flip-flops on men will never be universally loved—and that’s okay. They represent the fine line between effort and ease, taste and taboo. For every person who cringes, someone else calls it confidence. Maybe that’s the magic of fashion: the freedom to toe the line (pun fully intended). 

Also read: The 20 Best Halloween Costumes For Any and Every Type of Vibe in 2025

Also read: Biker jackets are back and cooler than ever