Here is how it happened: Jenna Lyons was at the Wing in SoHo in December 2021, giving an interview to a podcast called “Dyking Out,” having recently been advised that she wasn’t doing enough to represent her community of gay women.

“I felt really badly,” she said a year later, over avocado toasts at Sant Ambroeus. “That was never really something that occurred to me.”

So she did the podcast, and about an hour into the conversation, the interviewers pitched an idea: Ms. Lyons as a cast member on “The Real Housewives of New York City.”

“I’m down,” she replied: two words that may have changed her life.

Ms. Lyons, the former creative director and president of J. Crew, was an icon of early 2010s style. She was a high-low priestess, evangelizing sequins as day wear. She modernized prep, dressing Michelle Obama when she was the first lady — and therefore America.

In her crew neck sweaters and bright lipstick, Ms. Lyons served as a walking advertisement for a company at the peak of its success. It was not normal for fashion enthusiasts to recognize the head designers of mall brands, yet they knew Ms. Lyons. So did many casual shoppers, regularly browsing “Jenna’s Picks” on the J. Crew website.

But when she left the company in 2017, Ms. Lyons also left the public eye. She didn’t really return until late 2020, when she hosted a design competition show on Max for one season — a move into the reality TV world. Still, the announcement, last October, that she’d star on the upcoming season of “The Real Housewives of New York City,” drew much attention.

Ms. Lyons, 55, was known for being tasteful, aspirational. She’d been to the Met Gala seven times. The Housewives were a brawling pageant of guilty pleasure, redefining the cultural meaning of “housewife.” (Many of them were, in fact, divorced.) They were flamboyant, chaotic. Two of them went to prison.

And yet Ms. Lyons embraced the idea.

In February 2022, when another gay podcaster pasted Ms. Lyons’ face onto a promotional image of the “RHONY” cast, Ms. Lyons shared it on her Instagram story, writing: “Who do I need to call?? I am available.” It was a bit of a joke, she said, “one of those moments where somebody posits something that seems completely unlikely, and out of humor, I said yes.”

Still, she forwarded her post to Andy Cohen, the Bravo host and executive producer of the Housewives franchise, whose Christmas parties she had attended.

“You know what … this is a good idea,” Mr. Cohen replied via direct message. Ms. Lyons sent a tilted-head-laughing emoji. Then a dual-red-exclamation-point emoji. Then a heart emoji.

One month later, Mr. Cohen announced that Bravo was in the process of rebooting “RHONY,” which had lost viewers in recent seasons, with an entirely new cast. He wanted a new “multicultural group of friends” from “diverse backgrounds, races and religions” for its 14th season, he told Variety. Several months after that, Ms. Lyons got a call asking if she would do a screen test.

Of course she passed the test; Ms. Lyons has always been a compelling figure — slender and tall, with oversize glasses and a shirt often unbuttoned to her navel.

To be a Housewife, as Mr. Cohen said in an interview, is to be “funny, dramatic, outspoken, surprising.” (Wealthy is implied.) What made Ms. Lyons click for him was that you couldn’t look away from her. “When she comes on the screen, you want to see more of her,” he said. Even better for his revamp plans, “she’s a real player in New York.”

For her part, Ms. Lyons believed appearing on television could help advance her business pursuits, like her false eyelash brand LoveSeen, which she founded in 2020. Just being on the “Today” show one time led to an uptick in sales.

“We need the exposure,” she said. She also liked the idea of bringing some queerness to a largely straight franchise.

But one day, while Ms. Lyons was reciting this reasoning to a close friend, she said, the friend stopped her: “‘You want the attention,’” the friend said. “‘You don’t want to fade into oblivion.’”

And it was true, Ms. Lyons realized. After she left J. Crew, the fashion industry, once enamored with her, seemed to moved on. There were no enticing job offers, and fewer fancy invitations to draw her out of her newfound isolation.

“I really faded away,” she said. “It was such a big job, and I was well respected, and I had a big life in that way, and then it kind of all went away.”

‘You Cannot Hide’

Ms. Lyons and J. Crew may have separated in 2017 — it was a mutual decision, they said, after a few years of declining sales — but the two entities, together for more than 25 years, have never fully shaken each other.

Her attachment to design is still evident in the way she talks about color and fit, the technology and emotion of it all. She can spend 15 minutes deconstructing fuchsia, and more on the subject of swimsuit composition.

But she doesn’t miss her old job, she said. Between J. Crew and its sister brand Madewell and all of the categories they encompassed (women, men, children, bridal), she felt run down by the pace.

The expectation to design everything for everyone weighed on her. “There was always someone who was disappointed, who felt like we didn’t see them, that they weren’t represented,” she said.

She had cultivated a reputation in the media for being frank and unpretentious. She shared her insecurities about her incontinentia pigmenti, a genetic disease that caused balding, scarring and conical teeth. She cared about making fashion accessible and did not come from a wealthy background.

But by 2011, Ms. Lyons had also become a tabloid target. She was outed that year by The New York Post, which reported that she was not only divorcing her husband but also already dating a longtime female friend. Controversy erupted over her painting her son’s toenails pink.

When she left J. Crew, one narrative was that she’d sought too much of the spotlight, becoming “too big for J. Crew’s britches,” displeasingMickey Drexler, the chief executive of J. Crew and a retail legend. In 2013, a Fast Company cover story about Ms. Lyons had quoted the designer Todd Snyder — her friend and former colleague — as saying “they should just call it Jenna Crew.”

Maggie Bullock, who wrote a book about J. Crew, reported that when the Fast Company issue was released, a high-ranking executive at the company (not Mr. Drexler, who denied knowledge of these events) sent “a team of employees out to scoop up every issue they could find,” in order to lessen the impact of the story.

Still, in the last five years, neither J. Crew nor Ms. Lyons have achieved the same intoxicating heights of relevance they had reached together. (She appeared on three episodes of “Girls.” Beyoncé attended J. Crew’s first presentation at New York Fashion Week.)

Ms. Lyons has filled her days since with gigs: brand collaborations (jewelry, furniture, lipsticks), board appointments and some interior design jobs. In 2018, she announced a partnership with Turner Entertainment that yielded her one-season show, “Stylish With Jenna Lyons.” She joined Instagram in 2020, posting, in her first month, photos of her dog Popeye, some censored nudes and herself getting a lice treatment. After founding LoveSeen that year, inspired by her own lack of eyelashes, her career had some fresh momentum, but not to the extent she’d hoped. “My star is not big enough to support this brand on its own,” she said.

Ms. Bullock was still working on her book, “The Kingdom of Prep,” when the startling “Housewives” announcement dropped. It made some sense to her that Ms. Lyons was pivoting. After being “as central to the fashion conversation” as the designer had been at J. Crew, “how do you go back to anonymity?” she said.

But to Ms. Lyons’s ex-colleagues, “it was sort of an unthinkable thing, to join this other team,” according to Ms. Bullock. “People who had worked with her in the past were like: ‘Is she having some sort of mental break?’”

There are famous fashion people, like Ms. Lyons, and then there are famous reality stars, like Bethenny Frankel, NeNe Leakes or Lisa Vanderpump. They each have more than three million followers on Instagram; Ms. Lyons has about 275,000. She distinctly remembers one piece of advice imparted by Mr. Cohen while discussing the role: “‘All I can say is you cannot hide. Once you’re on the show, you cannot hide.’”

To some extent, Ms. Lyons still thought she could. After years of corporate leadership, she knew how to maintain her composure with all eyes on her. On her Max show, she said, she pushed back against producers who wanted her to be more brutally honest in judging contestants’ work. She thought she knew the landscape: Ms. Lyons said she was a devotee of the early seasons of “New York City,” and, when deciding whether to be part of the reboot, also watched recent episodes of “Atlanta,” “Salt Lake City” and “Miami.”

For her role as a Real Housewife, she told Bravo she never wanted a microphone on her teenage son, Beckett. “I don’t ever want him to look back on his time during this and be like, ‘I can’t believe I said that,” she said. “‘I can’t believe you didn’t protect me.’”

And before “RHONY” filming began, senior executives even called her to express their worry “that I was going to be too controlled on television,” she said.

“I am controlled,” she said in December, a few weeks into filming the show. We were at Sant Ambroeus, where, on a previous visit, she had subtly nodded to a young woman beside us eating alone with her phone, and made a motion with her hand to slightly lower our voices. In the era of DeuxMoi’s anonymous “spotted” texts, this was not an unreasonable suggestion.

“If you want me to not be controlled, if that’s what you’re looking for, I’m not the right person for you,” she said.

Best-Laid Plans

Cut to early April 2023, in the living room of Ms. Lyons’s apartment in SoHo, several weeks after the season had wrapped. All that control, she reflected, had kind of “backfired.”

“Out of hubris, or a sort of egoistic view of what I could handle, I was like, ‘Oh, I’ve got this, I’ve done this before,’” said Ms. Lyons, who had just realized she’d put her Celine lounge pants on backward that morning. (She decided to commit to it.) “When it really comes down to it, you end up being vulnerable, no matter how you slice it.”

Andy Cohen referred to this as “the process,” as in, “there’s no escaping the process.”

“I mean, you’re not drafted to be on the ‘Housewives.’ You either sign up or not,” said Mr. Cohen, who said that Ms. Lyons gets “really vulnerable.”

That does not mean she succumbed to certain clichés of the genre, Ms. Lyons said, like drunkenly screaming at castmates. (She has been sober for about two years.) But amid several moments she described as tense — arguments among the women over slights, real and imagined — she realized that by trying to “maintain a certain version of myself,” by keeping her guard up, she’d inadvertently created more tension.

In an early episode, for example, while the cast is sharing intimate details of their relationships, Ms. Lyons declines to talk about the woman she’s dating, causing at least one cast member to bristle. (“My life has put me in the public eye,” Ms. Lyons said, “and if someone does not want to be in that with me, then I have to respect that.”)

“That does not foster great relationships,” Ms. Lyons said.

Her dilemma could have been predicted by someone like Brian Moylan, the author of “The Housewives,” who has been recapping the series for almost a decade.

“Going on the show for your business is always a bad idea,” he said. It will certainly bring exposure; CVS stocks the hair care line of Kenya Moore from the Atlanta franchise, he pointed out. “But a lot of the women who go on for the sole purpose of promoting their business don’t want to pay the emotional slash reputational price that comes along with being a practitioner of the reality television arts and sciences.”

He thinks Ms. Lyons’s casting will help Bravo more than it helps her. “To give this reboot weight, they need someone with real New York City, cool, hip vibes to make the show real,” he said.

For Ms. Lyons, the group dynamic of the show ended up playing “on every insecurity that I have that I sort of forgot about,” she said, including, as a child, not being heard or accepted in large groups. People may have listened to her at J. Crew, but those were her employees. Her castmates didn’t have to listen to her.

That group included Sai De Silva, a content creator; Ubah Hassan, a model; Jessel Taank, a publicist; Erin Lichy, a real estate agent; and Brynn Whitfield, a communications consultant. While the new cast is more diverse in race and background than the previous “RHONY” casts, the women are still recognizably Housewives, competitively glamorous and outrageous. In a promotional image, they wore body-skimming black and metallic dresses that revealed their midriff, legs, cleavage; Ms. Lyons wore aviator eyeglasses, easy trousers and a white cropped shirt buttoned at just the collar.

To them, Ms. Lyons, older than all of them by at least a decade, initially came off as impenetrable. As one cast member, Ms. Lichy, says in a confessional: “Most girls in this group think that Jenna Lyons is a total enigma. She does weird quirky things, like she doesn’t like dill but loves parsley. She loves olives but not the black ones. She’s a little bit of an oddball.”

When the group spends a weekend in Sag Harbor, Ms. Lyons admits onscreen that she has never been on a girls’ trip.

“I’m nervous I’ll say something stupid. I’m nervous I’ll need alone time and everyone will be like, ‘What the hell, why?’” she says. After sharing with the group that her mother, who died earlier that year, struggled to make connections and was diagnosed with Asperger’s syndrome, Ms. Lichy comments that it “makes total sense to learn Jenna’s mom was very cold, because Jenna sometimes behaves that way.”

But that perceived coldness is at odds with moments in the first two episodes and trailer that reveal Ms. Lyons’s more spirited, sensual side.

She is shown kissing one castmate on the lips, grabbing another’s butt, and trying to form bonds through talking about sex. When the women gather at her apartment, she suggests an icebreaker game that asks questions like: “Are you dominant or submissive sexually?” During the weekend trip, she gives everyone lingerie.

This does not go over particularly well with at least one woman, who feels her lacy slip is unflattering compared with the others, and takes this personally. Neither does Ms. Lyons’s decision to host a party with a dress code that includes the color khaki, which the women seem to consider unsexy. (“I thought she was, like, done with J. Crew — why are we still doing khaki?” one cast member says.)

This dynamic is something Carolyn Bergier, a host of “Dyking Out,” saw firsthand, when Ms. Lyons invited her to a taping at the lesbian bar Henrietta Hudson. Cameras rolled as Ms. Lyons danced with a burlesque performer and was approached by a flirtatious TikTok model, Ms. Bergier said.

That night, Ms. Bergier asked Ms. Lyons how she was doing: “She’s like, ‘Oh my God. I’m so nervous, I’m so uncomfortable right now, I don’t go out and flirt with people.’” Ms. Bergier had heard another cast member mentioning that Ms. Lyons had been “a hard nut to crack” and “doesn’t tell us anything.”

“I hope she isn’t too closed off the whole season,” Ms. Bergier said. “I don’t want people to think that Jenna is not entertaining enough.” (Ms. Bergier added that she and her wife tried to make it into the episode filmed at the bar. “We both propositioned Jenna for a threesome,” she said. )

Ms. Lyons said she eventually did tell her castmates about her relationship, but only after it had ended, at a party celebrating one of their marriages. “Why did I just do that?” she wondered afterward.

“The words come out of your mouth, and you’re like, I can’t take those back,” Ms. Lyons told me. “It has not been the part of my life that I have been very successful in.”

In April, she had an update: “I currently have a massive crush on someone else.” In June, she confirmed that she was now dating her crush, the photographer Cass Bird.

‘Take Me Down’

One evening this spring, Ms. Lyons hosted an event at her apartment for the fertility start-up TMRW Life Sciences. It was a favor for a friend, the company’s chief executive, although Ms. Lyons occasionally rents out her space for small parties. Her interiors have been widely envied since the Brooklyn brownstone she used to live in appeared in Domino magazine in 2008.

There was a panel discussion about egg storage, a station for applying LoveSeen lashes, and a current Domino editor in attendance, who admitted she came partly just to see Ms. Lyons’s apartment. For women over 30, this is the power Ms. Lyons still holds: You visit her home to gawk at the Milo Baughman sofa covered in sunset-pink velvet, the Cy Twombly original poster on the wall, the open closet holding more than 300 pairs of shoes.

The best room, however, is one guests may not see: a half bathroom in the back of the apartment covered in memorabilia. Pinned to its walls are everything that might stick to an average person’s fridge, 10 times over: letters, Polaroids, handwritten notes, festival posters, red carpet credentials, her son’s middle-school certificates. On a table next to the toilet are awards statues and a disposable cup from the Obamas’ last White House party.

One of my visits coincided with that of a close friend of Ms. Lyons, Megan Kline Crockett, who runs the performing arts center at California State University, Long Beach. The two were planning to see a new performance by the choreographer Kyle Abraham, whose work is “the most beautiful, sexiest thing I’ve ever seen,” Ms. Lyons said, as D’Angelo pumped from her home speakers.

When they met at a dinner party 25 years ago, Ms. Lyons lived in a tiny place in Alphabet City, said Ms. Kline Crockett, a longtime fan of “The Real Housewives of New York City,” who didn’t learn about Ms. Lyons’s casting until she saw the news on Instagram.

She had been a little concerned at first. “I said to her, ‘I hope they’re nice to you,’” Ms. Kline Crockett said.

Ms. Lyons can’t deny that she is anxious, too. “I have a tremendous amount of fear around how I will end up looking, and at the same time, what can I do?” she said. “I can’t change anything at this point.”

Mr. Cohen, who had seen nine of the season’s episodes by the time we spoke, said he found her role “really interesting” and “different.” Earlier that week, a new trailer had shown a glimpse of an argument between the women, apparently over whether Ms. Lyons had declined to travel with the group because she didn’t want to fly coach. “Cast comes for Jenna Lyons in explosive trailer,” read the New York Post’s headline.

Bravo allowed me to visit the “RHONY” set once during filming, in February, while the crew captured Ms. Lyons on a photo shoot for LoveSeen. She gave direction to the models and makeup artists and photographer but kept the mood loose and warm, whipping around and laughing on set, often at her own expense. “This can kind of be used anywhere,” said a field producer, Michael Maniglia. “Everyone has their personal story, and part of her personal story is seeing her at work, doing her thing, being a boss.”

Mr. Maniglia and another producer rhapsodized over how they found her to be hands-on and competent and mindful — how some people might be intimidated by Jenna Lyons, but she was really so human. The crew had been on set for about four hours so far; they knew this scene would likely be cut to less than five minutes.

A few months later, I asked Ms. Lyons if she had any regrets about the way she had approached the show, which starts on July 16. She said she didn’t know yet.

“Maybe I’ll look nice. Maybe I’ll look smart. Maybe I’ll look stuck up,” she said. “Who the hell knows?”

“I’m nervous. I’m an easy target. I’m, like, an old white lady. Take me down. It’s fine.”