Cole Escola, the actor and playwright, stood before a mirror at a pastel-colored studio in Manhattan’s garment district, holding a spray of white satin flowers in one hand.
“The calla lilies are in bloom again,” Escola said, quoting a Katharine Hepburn line from the film “Stage Door.” The actor delivered it in Ms. Hepburn’s signature mid-Atlantic accent.
It was the last day of June — the day of the New York City Pride March — and Escola was at the studio of Jackson Wiederhoeft, the designer of the brand Wiederhoeft, 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 the former first lady Mary Todd Lincoln, portraying her as an alcoholic and an aspiring cabaret performer desperate to flee the White House and her husband. After it premiered Off Broadway in February, “Oh, Mary!” received a groundswell of raves from critics, generating buzz loud enough for it to twice extend its Off Broadway run before being brought to Broadway this summer.
The play’s glowing reception has made Escola an overnight sensation, 17 years after taking up acting. Previously, the actor had been known for YouTube skits and supporting roles on TV shows like “Search Party” and “At Home With Amy Sedaris.”
Escola’s newfound stardom has meant adjusting to certain trappings of fame, like being invited to late-night talk shows, awards shows and red-carpet events — and receiving the wardrobe scrutiny that comes with such public appearances.
“I feel like a bride,” said Escola, 37, who arrived at the Wiederhoeft studio wearing jeans, a T-shirt with a self-drawn graphic of Liza Minnelli and a red Willie Norris bag slung over one shoulder. “I’m having a fitting for my Broadway debut.”
“What a way to spend Pride,” added Escola, who identifies as queer.
To navigate the exposure, the actor for the first time has started working with a stylist: David Moses, 30, a former designer at Vaquera and other brands, who now runs a vintage and antique clothing business called Winning & Losing. Escola approached Mr. Moses this spring, not long after having been thrust into the upper echelon of the fashion world by attending the Met Gala for the first time.
Escola recalled the surprise of being invited to the gala after Anna Wintour, the Vogue editor in chief and the party’s mastermind, saw “Oh, Mary!” Off Broadway with her daughter, Bee Carrozzini, a theater producer.
“I don’t belong,” Escola recalled worrying after receiving the invitation. The actor grew up mostly in Clatskanie, Ore., a small town near the Washington border. “There are some rules I’m not going to know.”
After Escola told Vogue that a style inspiration for the gala was Miss Havisham from “Great Expectations,” the actor immediately regretted having made the suggestion.
“I thought, ‘Oh no,’” Escola said. “They are going to think, ‘Why does this stupid queen think they are going to wear a Halloween costume?’”
But Vogue staff members instead connected Escola with the designer Thom Browne, who dressed the actor in a white skirt suit and veiled hat — a look Escola described as Miss-Havisham-meets-Little-Debbie, with a dash of Pippi Longstocking.
“I am most inspired by individuality and confidence,” Mr. Browne said. “Cole is a true individual.”
Mr. Moses, who was a fan of Escola’s YouTube skits, was drawn to working with the actor for similar reasons. “I’ve always approached fashion with an element of humor,” he said. “Otherwise, it’s stale and boring.”
Mr. Moses’s 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.
“Anybody can pull a Dior look,” Mr. Moses said, referring to the types of high-fashion labels typically sought after by celebrity stylists. “But not everyone can get an antique clown costume.” (Plus: “Pagliacci,” the opera involving the relationships between a clown, his wife and her lover, was an inspiration for “Oh, Mary!”)
For the Drama Desk Awards last month, Mr. Moses put Escola in an archival blouse and skirt by Miguel Adrover, a Spanish designer whose fame crested in the early 2000s. With it, Escola wore an antique locket containing a photo of Mrs. Lincoln. For the “Las Culturistas” podcast’s Culture Awards, also in June, Mr. Moses dressed Escola in a corseted soccer jersey by Timothy Gibbons, a young Irish designer.
Many of the looks Escola and Mr. Moses come up with are developed by the actor giving the stylist prompts that sound like descriptions of characters that Escola likes to play in skits: “French wife of a C.E.O. coming for a facility visit,” for instance, or “Actress that is giving a news conference to deny she is having an affair with a politician.”
Escola has a penchant for ladylike jackets, pearls and other prim attire, a taste that the actor said was partially influenced by “maternal figures I looked up to” as a child, like Kanga, from the Winnie-the-Pooh stories, and Mrs. Potts, from “Beauty and the Beast.”
Wiederhoeft, a brand known for its archly feminine clothes, was at the top of Escola’s list of labels to wear to the Broadway premiere of “Oh, Mary!” The goal that night, Mr. Moses said, is for the actor to have a red-carpet moment on par with 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. “This is continuing that conversation.”
Indeed, Mr. Wiederhoeft started his namesake label 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 working with Escola because of the actor’s sense of humor.
Among the options prepared for Escola at the Wiederhoeft studio was a plumed white minidress from the brand’s fall 2024 collection. Mr. Moses arranged its feathers as Escola considered the dress.
“I think we need a pop of color, don’t you?” the actor said in a Miranda Priestly-esque inflection before reclining dramatically on a white settee.
A gold column gown made of embroidered fabric resembling snakeskin elicited oohs and ahhs. Escola pictured the dress on Bertha Russell — the new-money, pedigree-obsessed matriarch played by Carrie Coon on HBO’s “The Gilded Age” — or on a Titanic passenger.
“I would be first on the life raft,” Escola added. “Let’s let that be the guiding principle.”
After being tied into a gold lamé ball gown, Escola seemed to have found a top contender. “I feel like dollar-store Barbie,” the actor said. “Like when you want Disney Barbie, but your mom gets you the other one.” Escola compared trying on the gown to a scene in the fashion documentary “Catwalk,” when the designer John Galliano directs a young Kate Moss to show off a hoop skirt from his spring 1994 collection.
Later, Escola acknowledged the toll taken by the many appearances, rehearsals and performances that have happened since the actor began working on the Off Broadway production of “Oh, Mary!” in late January.
“I couldn’t be more tired,” Escola said with a noticeable rasp.
But the actor was well aware that fatigue is a price paid to be in vogue.
“It feels nice to be the belle of the ball,” Escola said. “I am taking it in while it lasts. Then my turn will be over and I’ll go to the back of the line again and hope that I get another turn.”
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