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Last Sunday at the twice-yearly Jazz Age Lawn Party on Governors Island, revelers bravely attempted to recreate 1920s cool in the face of hideous heat and humidity. There were men in boater hats, bow ties and suspenders; women wore bias-cut dresses and cloches while carrying parasols.

Standing in the center of Gatsby’s Garden, the event’s V.I.P. section, was Michael Arenella, the conductor of the headliner, Michael Arenella and his Dreamland Orchestra, and the festival’s founder.

But this was no “Great Gatsby” theme party. Mr. Arenella, in fact, takes issue with the book. “It painted a picture of frivolity, reckless abandon,” he said. “The era was more than that. The lucky few were able to live in a world of comfort, but most were hard-working people giving birth to the modern era, creating things with their hands and minds. Flippancy doesn’t resonate with me.”

Mr. Arenella, 38, said he was drawn to the “rebellion and exploration and freedom” of the era. “I am dedicated to the culture of the ’20s,” he said while sipping an elderflower and prosecco cocktail. “I was hungry for an opportunity to perform music in a setting that wasn’t shticky or schmaltzy, just outdoors on a sunny afternoon unfettered by technology.”

Mr. Arenella kissed cheeks and shook hands as he made his way through the crowd. A woman in a black beaded dress stopped him. “Can I interrupt?” she asked. “This is my first time here, and this is awesome. I came all the way from Toronto.” He smiled and replied, “As a half-Canadian, I thank you for being here today.”

His manners, like his clothes, are reminiscent of another era. At 6 feet 1½ inches tall, he is built like a strongman with broad shoulders, and most of his vintage-look clothing, including the white cotton suit he was wearing, must be custom-made.

His head is partly shaved, and a wave of curls cover part of his forehead; he has a mustache just slightly thicker than the one John Waters pencils on.

Growing up in Georgia as the child of artist parents, Mr. Arenella had a predilection for music and started playing trombone when he was 6. “I was fixated on anything old: a steam locomotive, gloves, it didn’t matter,” he said. “I felt like I was unearthing a piece of myself.”

“I do not own a microwave and I never will. Same goes for TV,” he said, attempting to define exactly how unfettered by technology he is.

He and his costume designer girlfriend, Analucia McGorty, 34, split their time between a cabin in Pennsylvania and an apartment in Red Hook, Brooklyn, where they do have air-conditioning. “We watch old movies on my computer, we have internet and email,” Ms. McGorty said. “We still have to live. We don’t eat period foods. I feel like that would be just aspic.”

The two met through his music. “She saw me for who I was, not an act but a real person,” he said. Has that been a problem in the past? “I guess I fit the mold for leading-man fantasies.”

For Mr. Arenella, music is a full-time job. His band plays 60 weddings a year, and so much of his time is spent transcribing 78 r.p.m. recordings by hand and practicing. When he relaxes, he does not put on sweatpants, nor does he even own a pair. “At home I’m generally naked,” he said. (He also doesn’t wear underwear.)

He left to conduct his band, while on the dance floor below the stage, people gamely attempted the Charleston (with mixed results).

After playing, he enjoyed a bare-chested ferry ride back to Brooklyn, where he changed into a red-and-white-striped shirt and khaki pants to meet a group of friends at Kittery, a seafood restaurant in Carroll Gardens. There were plates of fried calamari, Caesar salad and sliders spread over several adjoining tables.

“I’ve been starting to dress like this all the time,” said Steven Wong, 29, a dancer who performed at the festival. “I don’t have a girlfriend now, but I would like her to be into the ’20s. All the girls I like are into the ’50s.”

Adam Coren, a 26-year-old hat salesman and artist, said, “When I was 2, I made my mom buy me dress shoes instead of sneakers.” The comment was enough to spur a spirited discussion of Crocs.

“They can’t be sensible,” said John Veglak, who is in his early 50s and wore round eyeglasses and knickers. He noted that the group’s style of living was not made up purely of anachronisms. “There’s no block of ice for the refrigerator, no coal stove,” he said.

On the other side of the room, Mr. Arenella could be seen writing a text message on another outdated device: his flip phone.