The Many Roles of Wendé Gilmore

The owner of Vamped Up Vintage moonlights as an actress, writer and costumer for the Seminole Gulf Railway Murder Mystery Dinner Train

BY January 5, 2018

To Wendé Gilmore, all the world’s indeed a stage and she is certainly a player. And why not? There are so many fascinating roles to play.

Just look. Here we are at Vamped Up Vintage, Gilmore’s shop in Fort Myers’ Royal Palm Square. Fancy yourself a femme fatale? See yourself as a suffragette? Here’s someone who shares your vision—whatever it is—and who has been collecting vintage items for men and women for decades.

Today she’s outfitting Laz Padron, who with his fiancée, Jennifer Zappia, is going to a 1920s wedding in a few weeks. Music from the ’40s is playing.

Padron is occupied; he’s behind a curtain in the little dressing room, trying on checkered black and white trousers and vest with a burgundy shirt. So Gilmore talks about her start as a collector of historical fashion. “The first thing I bought was a 1940s suit for women,” she recalls. “A jacquard silk brocade. It was at the Goodwill or Salvation Army in Largo, for 50 cents!” she says. She was 14.

Padron emerges, looking pleased.

“So now you need a super-cool bow tie with that. And suspenders under that vest,” Gilmore says. She offers a hat.

Zappia pronounces Padron’s outfit “great.” And then asks, “But do you want a hat?” She’s clearly looking for a “no.”

He doesn’t. Undaunted, Gilmore offers another hat just in case, one pair of shoes (“from a wealthy man’s estate”) and then another, pulling out boxes and containers from different areas of the shop. But this is no hard sell. Clearly it’s a collaboration. You can see that this isn’t really costumery; it is the creation of a role to be played, and Gilmore is guiding him into that alternate world of Gatsby Laz.

For herself today, she is conjuring the 1950s, wearing a fern-colored reproduction dress with a cutout pattern at the neck and sleeves and low-heeled pumps. A straw mannequin nearby is wearing the same dress at this particular party. That’s harmless in this case, but not the goal for anyone Gilmore is outfitting.

Most garments are rented; some are sold. Padron will be in fine ’20s fashion for the wedding for about $150, accompanied by Zappia, who chose the first of seven flapper dresses she tried on here the weekend before.

“I do a lot of vintage weddings,” Gilmore says. “Seven last year. Gatsby weddings are huge right now.”

She can help re-create just about any time period. “Every decade … if I can dig in hard and get into it, I’m having a good day,” she says.

“To say I get immense pleasure from styling my clients in magnificent vintage attire would be a colossal understatement,” she writes on the Vamped Up Vintage website. “If only for a moment or an evening or for a lifetime, it is my pleasure to take you visually to another time and place.”

Her approach for herself seems to be a funky take on Dress for Success. For others, it’s RuPaul’s “We’re born naked, and the rest is drag.” Every day can be Throwback Thursday. Who are you today?

Many evenings, she’s a criminal.

That’s by her own design, too, as writer and costumer for the Seminole Gulf Railway Murder Mystery Dinner Train.

Onboard, she may be Carolina Baker, the mother of Pretty Boy Boyd, but don’t call her Ma. At least that’s what she says in The Not-So-Great Train Robbery, which ran from early September to late November several nights a week.

Gilmore played a great gun moll, hillbilly-style, an aw-shucksing but still glamorous takeoff on matriarch Ma Barker (of the Pretty Boy Floyd crime family legend—although show notes claim any similarities to a real situation or person are coincidental). In the play, Carolina Baker has recently married Fingers Flannigan, but the audience quickly finds out that’s no reason to get all sentimental on her behalf. Clad in a form-fitting flowered dress and a floppy hat, Baker declares, “Just fer the record, I don’t believe in dee-vorce, but I don’t have no problem being a widder.”

And just for the record, Gilmore herself would definitely have a problem with being a widder. She’s been happily married for two years to Bill Bowman. They met through an online site, first getting together at Twisted Vine Bistro about five years ago.

“I kinda fell for her the first time I met her,” Bowman says.

Gilmore was interested but reluctant. Previous relationships sometimes had been dramatic—and not in a good way.

They went on a few dates, including a gig with his band: classic rockers Vinyl Countdown. And then she got food poisoning and had to cancel a date. Bowman offered to visit, to bring something. No, she said.

He showed up anyway. Big mistake. He had gone backstage without being invited. She threw him out and that was it. For a couple of years. At first, he sent flowers and an apology, which she didn’t read because she threw the card away.

And then her photo popped up on Facebook or somewhere, he says, and he hadn’t forgotten about her.

“Meet at the Verandah?” he asked. “You can expect to buy me a really expensive bottle of champagne,” Gilmore recalls telling him, and laughs. He did. He apologized. They stayed for dinner. Six months later he asked her to marry him and she said yes.

“I see a person nobody else sees,” he says. “We’re both pretty crazy people, but … she’s very loving. And quieter at home. I’m probably the more vocal one when we go out.”

He is allowed backstage now. “I know her past, her fears, her weaknesses.”

Her past: Now there’s a story. Born in a small town near Buffalo, New York, Gilmore moved to Largo, Florida, at age 13 with her dad, a pressman—“he printed the funny papers all over the country back in the day”—and her mom, a secretary to the local vice president of Kraft Foods.

Gilmore graduated early, at 17, “with honors,” she says, “but academia just wasn’t my thing.” She moved to Tampa and worked for a trendy upscale dress shop. “I lived in a cool apartment upstairs in Hyde Park,” she says.

And then she heard that Barnum & Bailey Circus was hiring, went for an audition and was hired as a magician’s assistant.

“You just had to be willing to travel,” she says. “I was 18, almost 19, so sure. I always thought (the circus) was the corniest thing ever, but I loved it. You do have to be a little bent to do that, though.”

Gilmore laughed. “There are some real unsavory characters. Also some amazingly unique ones. It’s nonstop craziness. You have the animals, the dwarfs, the clowns, the aerialists, all with different ethnicities and mindsets.”

She described her four years touring—by train and plane and as far as Mexico City for three months, which she loved—as the best time of her life. It was dangerous, too. Being sawed in half and turned into a tiger are still risky tricks despite the aspects of illusion, she says.

And then she met a man in Laredo, which was “like a frontier town,” she says. She left the circus and they moved to Atlanta, where she worked in theater for years.

She got divorced, met another man, was ready to move to Los Angeles, where she had some connections, she says, and got pregnant. That was an “epiphany moment.” Despite less than ideal timing or circumstances, she thought, “I’m having this baby.” “And it was the best thing that ever happened to me,” she says.

“I credit him”—her son, Chrystopher Blackstone—“with saving me,” Gilmore continues. “I was the most selfish person on the planet. But when I had him, it felt like every selfish bone in my body left me.”

She and her son’s father divorced. Gilmore enjoyed a successful career in real estate. But then she hit a rough patch in life and decided to move with Chrystopher, who was 7 years old, to Southwest Florida. Her sister, Rhonnda Fabiola, lived here.

Fabiola is married to Jimmy Fabiola, who was a recurring character on the Tim Allen sitcom Home Improvement. The Fabiolas eventually moved. Gilmore stayed. Her son graduated from Full Sail University and is working in television.

Gilmore continued with theater and costuming here and now has been with the Seminole Gulf Railway dinner train for 10 years.

Her past lives give her plenty of material for the mysteries she writes for the company. Her large collection of vintage clothing gives her the means to outfit the characters. And somehow it all comes together.

She texts to me a group shot that included a man wearing large purple pants, suspenders and shoes with large, clown-type toes, and another man in bright stilt-walker pants and a tiny black hat with a flower on it. “These are probably the most unusual costumes I designed!” she writes. “Can you see the circus bleeding through? Lol.”

Related Images: