Leo Bloomfield has been the face of St. Augustine for a long, long time. For many years, day by day, Leo has walked the streets of the Oldest City in his famous green shorts, entertaining the public and spreading joy throughout with his witty comments.

“My name is Leo B. Bloomfield like what the flowers do and where they do it,” Leo said.


Leo on The Bridge of Lions

When you see Leo walking the streets, always equipped with a smile, whether you know him or not, he catches your eye. His persona is unmistakable. His classic green short shorts are iconic, his belt with the water bottle strapped to it sticks out, never bearing a shirt, always rocking a bushy gray beard, while rocking his eye patch proudly matching his black cowboy hat, Leo’s soul mission is to live life to the fullest and to put smiles on people’s faces.

“Here in St. Augustine, what I like to do is put smiles on peoples faces, make people feel better,” Leo said.

Whether a local resident, Flagler transplant or random visitor, Leo makes it a point to make people’s days a little better if he can. His contagious courtesy and genuine concern for other people’s well-being has become a part of the streets and sidewalks of St. Augustine.


Leo aiming to please.

He explained how it’s amazing to see the reaction he gets from others. How much he affects people’s attitudes when he is walking around town or when he entertains and brightens people up by telling jokes, showing what he said “the kids” call a gun show or performing 17th century Irish tunes.

Amber Sprinkle, a Flagler student and St. Augustine resident, saw one of these “gun shows.”

“He walked up to my car window once in a red towel wrapped around his waist and asked if I wanted to see the “gun show.” Obviously I said yes, and he flexed in front of me for a solid two minutes. Super uncomfortable but hilarious none the less,” Sprinkle said.
Above the subtle awkwardness he sometimes provides, it’s all about living life to the fullest, spreading good vibes and enjoying every single day Leo explained.

“Life is a mirror, whatever you send out comes back at you, you might only be going around one time, so you might as well make the best of it,” Leo said.

Leo walks the streets every day, shirtless as always, same green shorts catching your eye. It’s his thing.

“I’ve been walking forever,” he continued. “I enjoy walking, I walk about 10 miles a day, every day, but not all at once.”

Those famous green shorts, in which he has seven pairs of, are what he wears every single day, rain or shine, hot or cold.

“I wear the same outfit everyday all year long, the weather conditions it’s a matter of mind over matter, and if you don’t have a mind well, it doesn’t matter,” said the witty street walker.

Most of the time people catch Leo walking around the streets of downtown around St. George street or down A1A towards the beach. But sometimes, you can catch Leo at a local bar, blending with the crowd, as much as he can of course. He has become a hit with bar tenders and bar goers and almost a legend to the college folk.

Flagler students seem to be especially fond of Leo. He has many times been the subject of student documentaries, journalist pieces, essays and visual art projects, he has often been invited to house parties to hang with the bunch as well.

“I haven’t paid for an adult drink in about seven years,” Leo said when describing his experience with hitting the bar scene.

Alex Kellem, a 2012 Flagler Graduate, once dressed up as Leo for Halloween and wasn’t the first, or last, to do so. Recent Flagler Graduate and unaware classmate of Kellem, Jessica Reynolds, snapped a picture with Kellem that night and had this message to add.

“I don’t even know who this is, but Leo is such a legend kids dress up as him for halloween!”


Flagler Grads Alex Kellem and Jessica Reynolds laugh as Kellem dressed like Leo for Halloween a couple years back.

Recently, Brady Bigalke, another Flagler Graduate and co-founder of the production company NobleLight Productions, made a short film showcasing Leo as he explains his persona and his role in the city of St. Augustine. Since its posting on social media, the video has made its way around the Oldest City and has become a hit throughout the community.

Enjoy the clip and take a couple minutes to learn about St Augustine’s favorite character below.


Credit: Noble Light Productions: St. Augustine, Fla.