Cole Escola, the actor and playwright, stood before a mirror in a pastel-colored studio in Manhattan’s fashion district, holding a bouquet of white satin flowers in one hand.
“The calla lilies are blooming again,” Escola said, quoting a Katharine Hepburn line from the movie “Stage Door.” The actress delivered it in Ms. Hepburn’s trademark Atlantic accent.
It was the last day of June — the day of New York City’s Pride Parade — and Escola was at the studio of Jackson Wiederhoeft, the creator of the Wiederhoeft brand, for a fitting before a red-carpet appearance: the Broadway premiere of “Oh, Mary!”, a comedic play written by and starring Escola, on Thursday.
In the show, Escola plays a fictionalized version of former first lady Mary Todd Lincoln, whom she portrays as an alcoholic and aspiring cabaret performer desperate to escape the White House and her husband. After its Off-Broadway premiere in February, “Oh, Mary!” received an enthusiastic reception from critics, generating enough buzz that the play was extended twice Off-Broadway before coming to Broadway this summer.
The play’s warm reception made Escola an overnight sensation, 17 years after he began acting. The actor was previously known for his YouTube sketches and supporting roles on TV shows like “Search Party” and “At Home With Amy Sedaris.”
Escola’s newfound fame has forced her to adjust to some of the trappings of celebrity, such as being invited to late-night talk shows, awards shows and red carpet events — and to the sartorial scrutiny that accompanies such public appearances.
“I feel like a bride,” said Escola, 37, who arrived at the Wiederhoeft studio wearing jeans, a T-shirt with a drawing of Liza Minnelli that she had drawn and a red Willie Norris bag slung over her shoulder. “I’m having a fitting for my Broadway debut.”
“What a beautiful way to celebrate Pride,” added Escola, who identifies as queer.
To overcome the exposure, the actor began working with a stylist for the first time: David Moses, 30, a former designer at Vaquera and other brands who now runs a vintage and antique clothing company called Winning & Losing. Escola reached out to Mr. Moses this spring, shortly after he was thrust into the upper echelon of the fashion world by attending his first Met Gala.
Escola recalls the surprise of being invited to the gala after Anna Wintour, the Vogue editor-in-chief and the party’s organizer, saw “Oh, Mary!” Off Broadway with her daughter, Bee Carrozzini, a theater producer.
“I don’t belong in that group,” Escola recalled, nervously, after receiving the invitation. The actor grew up mostly in Clatskanie, Oregon, a small town near the Washington border. “There are certain rules I don’t know.”
After Escola told Vogue that the gala’s styling inspiration was Miss Havisham from “Great Expectations,” the actor immediately regretted making the suggestion.
“I thought, ‘Oh no,'” Escola said. “They’re going to be like, ‘Why does this stupid queen think they’re going to wear a Halloween costume?'”
But Vogue staffers instead connected Escola with designer Thom Browne, who dressed the actor in a white skirt suit and veiled hat — a look Escola described as a cross between Miss Havisham and Little Debbie, with a touch of Pippi Longstocking.
“What inspires me most is individuality and self-confidence,” Browne said. “Cole is a genuine person.”
Mr. Moses, who was a fan of Escola’s YouTube sketches, was drawn to the idea of working with the actor for similar reasons. “I’ve always approached fashion with a sense of humor,” he said. “Otherwise, it’s bland and boring.”
Mr. Moses’ first styling job with Escola was for an appearance on “The Tonight Show” in early June. He dressed the actor in an antique clown costume.
“Anyone can wear a Dior look,” Mr. Moses said, referring to the high-fashion labels typically sought after by celebrity stylists. “But not everyone can afford an antique clown costume.” (Also: “Pagliacci,” the opera about the relationship between a clown, his wife and her lover, was an inspiration for “Oh, Mary!”)
Last month, at the Drama Desk Awards, Mr. Moses dressed Escola in an archival blouse and skirt by Miguel Adrover, a Spanish designer whose fame peaked in the early 2000s. Escola carried an antique locket containing a photo of Mrs. Lincoln. For the Culture Awards of the podcast “Las Culturistas,” also in June, Mr. Moses dressed Escola in a corseted soccer jersey by Timothy Gibbons, a young Irish designer.
Most of the looks that Escola and Mr. Moses dream up are crafted by the actor giving directions to the stylist that resemble descriptions of characters Escola likes to play in sketches: “The French wife of a CEO visiting a factory,” for example, or “An actress who gives a press conference to deny she’s having an affair with a politician.”
Escola has a penchant for ladylike jackets, pearls and other sensible attire, a taste that the actor says was partly influenced by “the mother figures I looked up to” as a child, such as Kanga from the Winnie the Pooh stories and Mrs. Potts from “Beauty and the Beast.”
Wiederhoeft, a brand known for its decidedly feminine clothing, topped the list of brands Escola was to wear to the Broadway premiere of “Oh, Mary!” The goal of the evening, Mr. Moses said, is for the actor to have a red-carpet moment comparable to Escola’s Met Gala debut.
“The Met was one of the first times Cole wore something that was truly a work of art,” he said, referring to Escola’s white Thom Browne ensemble. “It allows for that conversation to continue.”
Indeed, Mr. Wiederhoeft launched his namesake brand after working for three years at Thom Browne. Like Mr. Moses, Mr. Wiederhoeft, whose brand is a finalist for this year’s CFDA/Vogue Fashion Fund Award, said he was drawn to Escola because of the actor’s sense of humor.
Among the options prepared for Escola at the Wiederhoeft studio was a white feathered minidress from the brand’s fall 2024 collection. Mr. Moses arranged its feathers while Escola examined the dress.
“I think we need a splash of color, don’t you think?” the actor said with a Miranda Priestly inflection before dramatically reclining on a white couch.
A gold-column dress, made of an embroidered fabric resembling snakeskin, elicited “oohs” and “ahs.” Escola imagined the dress on Bertha Russell — the pedigree-obsessed, newfound wealth matriarch played by Carrie Coon in HBO’s “The Gilded Age” — or a passenger on the Titanic.
“I would be the first one on the lifeboat,” Escola added. “Let that become our guiding principle.”
After donning a gold lamé ball gown, Escola seemed to have found a worthy suitor. “I feel like a dollar store Barbie,” the actor said. “Like when you want a Disney Barbie, but your mom gives you the other one.” Escola compared the dress fitting to a scene from the fashion documentary “Catwalk,” when designer John Galliano asks a young Kate Moss to show off a hoop skirt from his spring 1994 collection.
Escola later acknowledged the toll taken by the many appearances, rehearsals and performances that have taken place since the actor began work on the Off Broadway production of “Oh, Mary!” in late January.
“I couldn’t be more tired,” Escola said, her voice hoarse and audible.
But the actor was well aware that fatigue is a price to pay for being fashionable.
“It’s nice to be prom queen,” Escola said. “I’m enjoying it while it lasts. Then my turn will be over and I’ll go back to the back of the line hoping to get another turn.”