Scooting around Hawaii last week, President Obama broke one more historic barrier by setting a new benchmark for the limits of presidential casual wear.

He was wearing flip-flops.

Historians agreed it was the first time they could remember seeing the leader of the free world snapped in a public setting, wearing nothing more than a flimsy strip of rubber on his feet.

While Ronald Reagan was famously snapped strutting on his way to Camp David in his cowboy boots and John F. Kennedy was no stranger to sailing in his deck shoes, the picture of Obama tooling around an ice-cream shop with his toes on full display seems be a first for the presidency.

“I can’t say I’ve seen a president’s toes before. This could be a very usual thing,” said presidential historian Jane Hampton Cook, author of an upcoming children’s book “What Does the President Look Like?”

“But I don’t think this is a big deal. Your footwear belongs to the occasion. If you’re on the beach buying your daughter snow cones, I don’t think you can beat him up for this. Now if he’s wearing flip-flops to the State of the Union, that’d be different.”

Presidential historian Doug Wead concurred.

“In public, no. I haven’t seen the president’s toes,” he deadpanned.

And while most historians couldn’t think of an example of presidential appendages being on such display, most agreed it wasn’t necessarily the worst thing in the world.

Richard Nixon famously came off like an uptight weirdo because of his bizarre habit of walking along the beach in his formal wingtip shoes, so Obama’s choice of the casual summer staple could be a good thing.

“It makes him look like a man of the people, and they [his advisers] probably like that it’s an informal and inexpensive shoe,” Wead said.

But times have changed.

Wead recalled a time when he was at Jimmy Carter’s White House for an event, and some young people wore sneakers.

“I remember Mrs. Carter looking down at their feet, horrified.”

Fashion expert Meghan Cleary agreed.

“I can think of no other president photographed in flip-flops,” said Cleary, author of “The Perfect Fit: What Your Shoes Say About You.”

“[George W.] Bush wore cowboy boots a lot, even to formal occasions,” she said. “I am guessing other presidents may have worn flips but didn’t get a pic snapped in them since the press was probably more tightly controlled and there were not so many media sources.”

Not everyone in the Beltway appreciated Obama’s hang-loose approach to footwear.

“You don’t think you’re going to see [Russian Prime Minister] Vladimir Putin wearing flip-flops, do you?” said one DC observer.

As presidential fashion firsts go, Obama’s flip-flops in public probably won’t have the same impact that previous attire milestones have had for other inhabitants of 1600 Pennsylvania Ave.

Obama may even flirt with political danger by donning the wimpy footwear, experts say, but he will likely survive.

“If you were born in Hawaii, if you grew up in Hawaii, if you vacation in Hawaii and you don’t wear flip-flops, then there is something seriously wrong with you. You don’t wear wingtips to the beach in Hawaii,” said Kathleen Hall Jamieson at the University of Pennsylvania’s Annenberg Center for Public Policy.

Also, Obama has already pushed the envelope plenty in the footwear department.

As a candidate, Obama was snapped in 2008 wearing flip-flops while vacationing with his family in Honolulu.

And last year, the commander-in-chief set out wearing sandals for a trip to DC’s International Spy Museum with his daughters.

But Obama is not the first president to get caught up in the sensation of flip-flops.

“During the flip-flop scandal of 2005, a bunch of lacrosse girls wore flip-flops for the formal occasion of meeting President Bush and getting their picture taken,” recalled Cleary. “This was a no-no because of the occasion.”

“It was very much a generational thing, since the girls thought nothing of it,” she said. “They wore them all the time on campus and thought it was perfectly fine.”

And it was the excitement among that very generation on college campuses across the country that carried Obama into the White House three years later.

Additional reporting

by

David K. Li