NEW YORK—Preston Bailey has planned some of the most elegant weddings in extravagant places: the middle of a desert, Donald Trump’s golf course, and once even in an airborne plane.
Today, while millionaires and billionaires—such as Oprah Winfrey, Donald Trump, and Catherine Zeta Jones—have hired him to create unique and beautiful weddings, in his youth Bailey had not planned on planning weddings.
He recalled his first wedding in the ’70s. It was a Jewish wedding. He had no idea what a chuppah was and had to do research on the wedding ceremony canopy.
“At the time there was no such thing as a wedding planner, lighting, or designers, it was merely a matter of finding a few center pieces and a bouquet,” he said.
As a Panamanian immigrant, Bailey began planning weddings to pay the bills.
Growing Up in Rural Panama
Bailey grew up in a modest house in the middle of rural Panama. He and his four siblings never starved, but they didn’t have quite enough to eat either.
He would wear his brothers’ hand-me-downs. There was no likelihood of fashion and design occupying his mind.
After he dropped out of high school, talking about his mother Bailey said, she “had a moment of genius when she decided to send me to New York. … She said ‘Who knows what will happen to you if you stay here.’”
His sister, who was a nurse in New York, sponsored him to immigrate.
Without a clue of what he was going to do, Bailey arrived in New York in 1969 at age 19.
He took an evening accounting class at Pace University, but he didn’t finish the semester. “I had no interest in numbers,” he said.
He managed to work as a bank clerk for two years, before a fateful friendship with a photographer led to a modeling career.
From 1972 to 1980, Bailey appeared on billboards and African-American magazines such as Ebony.
When his modeling career faded, an interior designer friend asked Bailey to help arrange flowers for his clients. From there, Bailey went on to arrange flowers for friends’ weddings and anniversary parties.
One thing led to another, and Bailey’s weddings soon became popular due to his ability to transform mundane spaces into monumental, theatrical settings.
He finds inspiration from nature and from his memories of the Panamanian rainforests.
In 1998, he used 30,000 white flowers to create a winter garden ambience for producer Melissa Rivers.
In 2010 he planned a wedding for a royal Middle Eastern family with 1,500 guests, and built a pavilion from scratch in the desert.
To this day, he sometimes runs into clients from as far back as 25 years ago who tell him they remember their wedding night as one of the most magical evenings of their lives.
“It means a lot to create memories that last a lifetime,” he said.
Bailey is known for his awe-inspiring ceiling treatments, from a ceiling that resembles a starry night to one with an upside down French garden hanging from above.
He creates these extravagant events with just a four-person team that has been carefully selected. They can handle planning only one wedding per month.
“I have a simple rule: if you can teach me something I’ll hire you,” he said. “We have developed a great bond, great way of encouraging and inspiring one another.”
Bailey describes each event he plans as a “life changing experience.” He said he learns a lot from his highly successful clients.
“When I was poor, I used to think that rich people just relaxed all the time,” he said. “But they’re incredibly hardworking and disciplined.”
“I emulate their qualities. I learn from them, what books I should read,” he said. “I never got a formal education, but I learn this way.”
Change and Growth
Bailey describes his work as creating dreams, but he is also a practical man.
“Sometimes it works, sometimes it doesn’t and you just have to learn to accept that,” he said.
Despite such high expectations and at times failed experiments, Bailey always carries himself with dignity and tranquility.
He said he is able to remain calm during moments of high-level stress because he doesn’t see himself as the most important person. “I remind myself that it’s just an event, I’m not a heart surgeon,” he said.
“It is important to be gentle to yourself when things go wrong,” he said.
After 33 years of experience in the wedding planning industry, Bailey is thinking of getting more involved in art direction.
He was recently an art director for a small film, and is now setting time apart to look into that more.
He feels the most important thing in life is to keep learning and growing.
“I’m 64 years old, but I’m still growing and changing,” he said. “If I’m learning something new, then it means that I am alive.”