The Stunning Transformation Of RHONY Star Jenna Lyons

Jenna Lyons doesn't mind admitting that she likes attention. She's a style icon, a fashion designer, a reality TV star, and more. She told The New York Times, "In all honesty, there is nothing more sweet and moving than when someone comes up to me and says: 'You're Jenna Lyons, aren't you? I love J. Crew.' That is so nice. I love that."

However, she's also bristled at her life in the spotlight. The star has been subjected to intense criticism from certain parts of the country, and while she likes being lauded for the creative work she does, she seems uncomfortable with the press' interest in her personal life. "I keep my sunglasses on," she told the newspaper of her strategy for avoiding watchful eyes when it all gets to be too much. She added, "Too bad I'm six feet tall."

Lyons has gone through many stages over the years, from an awkwardly-tall teen who turned to fashion to fit in, to a red carpet queen whose looks get people talking. Here's everything we know about the stunning transformation of "Real Housewives of New York" star Jenna Lyons.

Jenna Lyons was born with a genetic disorder called incontinentia pigmenti, a condition that affected her hair, skin, and teeth. This led to bullying, including an incident where she overheard girls behind her at an assembly laughing at the bald spot on the back of her head. This also came as news to a young Lyons, who had never been told about her condition by her parents. "Until that school assembly, I had no idea I was different from anyone else," she recounted in an essay for Oprah Daily. "My mom ... had pretty severe Asperger's and had trouble forming emotional connections. That day, she told me about my disorder, and then we basically never talked about it again."

Lyons dealt with the effects of her disorder and was also very tall as a child, both of which incited teasing from her classmates. However, they also led Lyons to a transformative discover in her life: Finding fashion. She told The Guardian that once she began dressing herself, she noticed that people's reactions to her would change. "[My condition] made me introverted, but it was also the reason I loved fashion, because it can change who you are and how you feel, and that can be magical." She also shared that when her grandmother got her a subscription to Vogue, it helped set her life path. She recalled, "That was when I knew I wanted to be a part of it."

After realizing as a teenager that she wanted to go into fashion, Jenna Lyons went to Parsons School of Design for undergrad. While there, she picked up an internship with designer Donna Karan. On the "Behind Her Empire" podcast, Lyons explained, "I didn't come from money, and, you know, the reason I was able to go to Parsons — it was an incredibly expensive school — was because I was an in a car accident, and I got a settlement from the car accident."

She enjoyed her experience working at Donna Karan, but Lyons still found herself being priced out of the fashion world she was hoping to break into. "Back then — this was 1990 — a jacket back then was $2,200. That was an exorbitant amount of money at the time, and for me. I couldn't afford to wear any of the clothes." The internship was unpaid, and while she found people were impressed by the brand's name, no one she knew had any personal connection to the because it was too aspirational. "I couldn't afford to do the job," she recalled.

So after graduating from Parsons, Lyons decided to work with a brand that was much less high-fashion, and much more approachable. That choice would soon come to define her career, because right after college, Jenna Lyons found J. Crew.

Jenna Lyons' first role at J. Crew was at the bottom of a long ladder of assistants. However, she worked her way up, and by 2010 she held two separate but equally important titles: President and Executive Creative Director. "What it says is that no financial decision weighs heavier than a creative decision," she told Fast Company of her dual role. "They are equal." Lyons' hard work took J. Crew from a preppy mall brand to a respected name in the industry, and a certain famous face helped make it all happen.

Michelle Obama wore J. Crew numerous times as the First Lady of the United States, and the attention she brought to the brand helped Lyons' own popularity skyrocket. While the company was unaware she would be wearing their clothes during a 2008 appearance on "The Tonight Show with Jay Leno," just a few years later, Lyons was all-in on styling the First Lady. During Barack Obama's 2013 inauguration, FLOTUS once again wore J. Crew. "It's an incredible part of American history and to be a part of it is probably one of the most poignant honors I can imagine," Lyons told USA Today.

Thanks to Lyons' influence on the Obamas, as well as her own reputation as an icon of "high-low" fashion, The New York Times gave Lyons a nickname that would follow her over the following decade. After 20 years at J. Crew, she had become "The Woman Who Dresses America."

As Jenna Lyons' position at J. Crew grew into a larger role, that meant more resources and freedom in Lyons' personal life. She was able to explore other passions, and it turns out Lyons isn't just a clothing designer; she's an interior designer, too. "I renovated a brownstone," she recalled on an episode of "The Real Housewives of New York City" (via Peacock). "And ironically, I got more attention for that than I did for my career in fashion."

Though Lyons might be exaggerating for effect, the renovated brownstone did indeed bring her a flurry of press. In 2008, Domino Magazine featured her renovated home on the cover. She showed off classic pieces alongside unexpected elements, bringing a similar high-low ethos to her interior design work that she brought to the fashion world. "Everything is so predictable!" She told the magazine. "We don't need to be so predictable. Instead, be inspired by something unique."

The designer later flipped the home amid her divorce. But while she initially purchased the brownstone for $1.4 million, she sold it in 2012 for $4 million. Not too shabby!

In a 2011 J. Crew advertisement, Jenna Lyons was pictured painting her son Beckett's toenails. In the ad copy, Lyons said, "Lucky for me, I ended up with a boy whose favorite color is pink. Toenail painting is way more fun in neon." Unfortunately, certain people in the conservative media sphere weren't having it. Dr. Keith Ablow wrote an op-ed for Fox News blasting the photo, writing, "It may be fun and games now, Jenna, but at least put some money aside for psychotherapy for the kid."

The backlash was so severe that it caught the attention of Jon Stewart, who discussed it on "The Daily Show." In a segment called "Toemageddon," the comedian shot back at critics of Lyons' photo. Quoting "Today" host Tamron Hall, he joked, "'What a mom is doing with her young son?' You make it sound like it's a story about incest or cannibalism!"

Speaking with New York Magazine, Lyons explained that her son simply wanted to copy her. "My God, my toes went from white to hot pink," she recounted. "It was very exciting." She reflected on the ad via Instagram in 2023, writing that her son was all grown up. She shared, "[He] still likes pink – and for those of you who think the color pink can turn someone gay – do a little reading – pink was originally a color designated for boys – and it didn't hurt them."

In 2011, Jenna Lyons divorced her husband, Vincent Mazeau. At the same time, she began dating a friend named Courtney Crangi. One night they got dinner together, and apparently, someone told the New York Post about it. The next thing Lyons knew, she got a phone call at work from the Post, asking whether she wanted to confirm or deny the rumors that she was seeing a woman. Before she knew it, Lyons had said the word "confirm." As she recounted in an essay for The Cut, the experience felt violating. "There's a special place for the person who took it upon themselves to make that decision," Lyons penned about her beef with The Post, adding that she had yet to come out to anyone in her life when the story ran. 

She later told "The View" that she didn't like the attention. The day the New York Post story dropped, she did whatever she could to prevent people from reading it. She took a cab around Manhattan, purchasing every copy of the Post she could find. "I didn't expect anyone to care about what I was doing in my personal life," she said. "All [of a] sudden, everyone cared."

Nowadays, Lyons is out and proud. "I do feel less responsibility to explain," she wrote for The Cut. "I don't feel like it's my job to make it clear for anyone else what's going on with me sexually or romantically."

Jenna Lyons is no stranger to wedding fashion. In fact, when she married Vincent Mazeau in 2002, she designed her own dress. She told New York Magazine that the embroidery in the dress depicted "leaves, flowers, and pheasants," and in a separate interview with the outlet, she explained that she had to design her own dress because there simply weren't any boutique options that matched her vision. "I wanted a triangle top with tiny straps and a full skirt, and there was nothing out there like that," she said.

More than a decade later, it was Lyons' fashion as a wedding guest that made headlines. She attended the 2014 nuptials of Solange Knowles and Alan Ferguson, turning heads in a feathered ensemble. She told The Cut that it was the same feathered skirt she'd worn to the Met Gala, but this time she paired it with a top and coat that brought the whole look together. The whole thing also happened at the last minute. "The T-shirt went on, the T-shirt did not work," she recalled. "The T-shirt came off. Another shirt went on that didn't work, and then the other shirt that went on and the coat went on, and then we went out the door." Lyons added, "I'm shocked that that outfit got that much attention, because it did not feel like I pulled it together very well."

After working at J. Crew for almost three decades, Jenna Lyons left the company in 2017 amid years of declining sales. The Obama years were over, the hype had faded, and the company wasn't doing as well as it once had. In an interview with Business of Fashion, CEO Mickey Drexler revealed, "Jenna [Lyons] and I got together and we both agreed it was time for a change." They've insisted it was a mutual decision ever since. Lyons told The New Yorker the same thing, recalling that it had been difficult to find the right moment to step away. However, she explained, "I'd been there for so long that I feel like I'd got to the point where I was no longer as effective as I'd wanted to be."

After leaving the company, Lyons was surprised to find that more than just her job had changed. No longer being connected to such an iconic fashion brand meant that her social status shifted as well. She told The New York Times, "I really faded away. 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." Up next for Lyons, however, was yet another transformation.

Now that Jenna Lyons is out and proud, she's been dating around. According to an episode of "The Real Housewives of New York City," she was set up on a date with "Schitt's Creek" star Emily Hampshire several years ago. "We didn't have a love connection, but we had a friend connection," Lyons recalled in a confessional interview. "Emily's been one of my biggest supporters."

Nowadays, they remain great friends. In 2022, Hampshire posted an Instagram photo to mark Pride Month. "#happypride NYC," she wrote. "I've moved into @jennalyonsnyc closet." The photo shows Hampshire reclining on a couch, sandwiched between Lyons' massive shelves of shoes. (The "closet" metaphor, of course, seems tongue in cheek.)

Hampshire has also spoken about the former J. Crew boss on the "In Her Words" podcast (via YouTube), sharing that her friend taught her how to be more confident. Hampshire said she's even encouraged Lyons to write a self-help book, warning her, "If you don't wanna write a book, I'm just gonna, like, print out our texts." Lyons is now helping Hampshire with a home renovation, though Hampshire said that she initially didn't feel confident verbalizing her own wants and needs. "I think just that fundamental thing of feeling entitled to what I want, as a woman, wasn't instilled in me," Hampshire reflected. Now that she's got Lyons in her corner, of course, all of that has changed.

Because of her incontinentia pigmenti, Jenna Lyons has had unusual teeth her whole life. "I grew up with horrible teeth and horrible teasing," she wrote on Instagram in 2022, sharing photos of herself as a child and X-rays of her teeth. "I didn't smile – ever – covered my mouth." In an essay for Oprah Daily, she explained that she got veneers in tenth grade. Until then, she recalled, "I only had about 13 very small, cone-shaped teeth, and huge gaps in the rest of my mouth."

As an adult, Lyons decided to get extensive reconstructive surgery as a preparation for tooth implants. "My upper teeth were the most complicated because my upper jaw bone had completely receded, especially on the left side. My nose was slowly collapsing because of the lack of bone," she wrote. The necessary surgeries have taken longer and been more extensive than she initially prepared for, and it's been more than six years since she started working on her smile. "I literally could have bought a house with what these teeth cost me, and I still have a way to go," she wrote.

In 2022, she shared via Instagram that her struggles with her teeth were finally nearing the end. After shouting out her doctors and people who helped with her recovery, Lyons credited one more person with her new smile — "@juliannemoore for the teeth inspo !!!"

After leaving J. Crew, Jenna Lyons embarked on a new phase of her career: Television stardom. She announced in 2018 that she was developing a reality show about her life after leaving the fashion house, telling The Hollywood Reporter, "I'm excited to be doing something totally different ... I've realized it's ok to be a little scared to pivot. Particularly in this day and age where everyone is trying to picture everything so perfect, I have found a great level of comfort in being honest with the fear."

The show materialized two years later, as she hosted "Stylish with Jenna Lyons" on HBO Max. Lyons was in the early days of launching her own company, and the show was designed around her search for an assistant. Contestants competed in challenges that ranged from hosting a dinner party to designing a monochromatic outfit — basically all the necessary skills you'd need a Jenna Lyons employee. She told Vogue it was important to her that the reality show be really real because she genuinely wanted to use it to find talent. "I didn't want to fake it or create drama that isn't there, and I wanted to give people real challenges," she said. "If I'm going to hire someone, I want to see what they can actually do."

Unfortunately, the show wasn't a hit. And not only was it cancelled after one season, but "Stylish with Jenna Lyons" has been removed from Max entirely.

One of the side effects of incontinentia pigmenti, the condition that Jenna Lyons was born with, is a lack of eyelashes. Lyons aimed to rectify that by launching a false eyelash company called Loveseen. She told Harper's Bazaar that her experience using other products made her the perfect person to found a brand like this. "I'm keenly aware of how transformative eyelashes can be and how they can impact how people see themselves and how others see them," she explained. "I thought maybe this could be a sweet spot for me." The line launched with 10 varieties, which Lyons' team designed and tested to work with any eye shape.

Lyons brought Loveseen to "The Tonight Show," telling host Jimmy Fallon just how effective her products were. When she applied an eyelash to Fallon's eye, he joked that he liked the way he looked with just the one. "This feels natch!" he said, to much audience laughter. "I like it."

The former J. Crew head's involvement in her new beauty company led to a new venture into reality TV. She told The New York Times that bringing Loveseen to a wider audience was a major reason she would soon be joining the cast of Bravo's "The Real Housewives of New York City." Putting it as simply as possible, Lyons stated, "We need the exposure."

At first, the idea of Jenna Lyons being a cast member on "The Real Housewives of New York City" was something of a joke. According to The New York Times, a fan photoshopped Lyons' head onto a poster for the show, and the style icon shared it on Instagram. Bravo producer Andy Cohen replied, "You know what ... this is a good idea." Cohen told "Today" that Lyons still took some convincing. "We had a few long conversations. Come-to-Jesus conversations, as they were," Cohen explained. "And Jenna went in for the trust fall, and I'm so glad she did, because she is a brilliant Real Housewife."

Season 14 of "The Real Housewives of New York City" premiered in July 2023, with Lyons as the most well-known member of a brand-new cast. She discussed being an openly gay housewife on "The View," saying that when she was at J. Crew, she would often hear from young people whose parents were afraid that being gay would limit their futures. "Those things just aren't true," Lyons said, noting that she's happy to be an example of a gay person who is "thriving." She added, "[Representation] gives a lot of parents who are scared a little more confidence."

Though one hallmark of the "Real Housewives" franchise is cast members' willingness to embarrass themselves on television — often revealing their personal lives on camera in excruciating detail — Jenna Lyons has chosen to keep a lot of details close to the chest. In an early episode from Season 14, Lyons was asked by her fellow castmates whether she was dating anyone. She replied (via People) that she was indeed seeing someone, but she didn't want to say more. "Because I've had so much press, I am very quiet about that, so I'm not sharing that," she said. She elaborated on her choice in a confessional interview, telling producers, "My life has put me in the public eye for my job and other things I've done. And that is my choice. And [if] someone does not want to be in that with me, then I have to respect that."

A few episodes later, however, Lyons confessed to the other "Housewives" cast members that she was going through a breakup (via Peacock). Her co-star Sai De Silva asked, "Do you think it was because this person wanted to be more vocal? Like, more seen?" Lyons confirmed that it was the opposite. "Jenna's finally opening up," De Silva said in a confessional, praising her friend for being more vulnerable in their friendship — and therefore on television — than she had been previously.