The Complete Transformation Of Monica Lewinsky

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The name Monica Lewinsky used to be synonymous with the cheating scandal that put her in the limelight in the '90s, when she was just in her early 20s. "Overnight, I went from being a completely private figure to a publicly humiliated one worldwide," she said in a 2015 TED Talk. "Granted, it was before social media, but people could still comment online, email stories, and, of course, email cruel jokes. I was branded as a tramp, tart, s—, w—-, bimbo, and, of course, 'that woman.' It was easy to forget that 'that woman' was dimensional, had a soul, and was once unbroken."

While the years she spent in the White House undeniably marked her life forever, the truth is that today, Lewinsky's name is no longer an instant reminder of her past. Over the past two decades, the former government assistant became a beloved activist, producer, podcaster, and fashionista — and her journey has truly been remarkable. Not many have managed to shed the impact of a scandal as big as the one Lewinsky had to deal with in her 20s, which is why it's even more impressive that, today, she is living proof that women have the power to change the narrative. Allow us to take you on a journey filled with growth, change, and plenty of stunning fashion moments.

When former President Bill Clinton's affair with Monica Lewinsky became public knowledge, the 24-year-old former intern's life completely changed. Not only was she instantly known as the woman who caused havoc in the marriage of the most powerful man in the world, but she also quickly became portrayed as the one who was responsible for the scandal. The age and power imbalance in their relationship didn't play a major role in the eyes of the media at the time, and Lewinsky was the one who publicly carried the majority of the blame. 

"Coming out of '98, I lost my anonymity, I lost my future, I lost my sense of self, I think I lost trusting myself in many ways," she admitted on an episode of her podcast "Reclaiming with Monica Lewinsky" in 2025. "I fell in love with D.C. and the White House and the job and the environment and then, very unfortunately, I fell in love with my boss who was married and also the most powerful man in the world. What followed was an inappropriate relationship that lasted for two years."

With the scandal, Lewinsky became a very photographed person, and while she was suffering internally, she didn't let it show. Lewinsky's aesthetic was the perfect example of what preppy style in the 1990s looked like — high necklines, classic patterns, and a very voluminous blowout were daily staples. In fact, the slightly oversized blazers that Lewinsky loved are a major '90s basic that came back in 2024. Even though she was living through the worst period of her life in a very public manner, Lewinsky remained put-together for the photographers, ensuring they never caught her off guard or in a more casual getup.

As the new millennium was about to kick off, Monica Lewinsky decided it was time for her to share her story. The former government assistant helped publish the book "Monica's Story," written by Andrew Morton (known for his work on the biography of Princess Diana). In 1999, Lewinsky did the infamous tell-all interview with Barbara Walters, in hopes of sharing her experience. "I really feel the worst about what this has done to my family and friends," she told Time in 1999. "And then I think second to that would be Chelsea and Mrs. Clinton, and I do feel bad about my part in how the country has had to deal with this. I made a lot of mistakes." 

Also for Time many years later, feminist author Leora Tanenbaum revealed that Lewinsky didn't really stand a chance against the media at the time. "It was a different time back then," she noted. "There was no consciousness raised about s—-shaming. Bullying wasn't even in the vernacular. People who were decision-makers and influential writers were making comments about her hair and body. It was a textbook case of the sexual double standard."

While making herself known as more than just the woman with whom former President Bill Clinton had an affair seemed impossible, Lewinsky wasn't giving up. The world of fashion and beauty seemed to spark her interest, and she used the opportunity to release her own handbag line, The Real Monica. In 2001, Lewinsky attended the Vanity Fair Oscar Party, proving she didn't fear red carpets — in fact, she walked them effortlessly. Around this time, Lewinsky's look underwent a subtle change as she parted ways with shoulder-length hair and embraced long layers. Fashion-wise, she stuck to preppy looks, but a subtle shift towards more experimental clothing pieces was noticeable.

In the mid-2000s, Monica Lewinsky decided to take a break from the U.S. spotlight and move to London, England, to pursue her education. In 2006, she got her master's degree in social psychology from the London School of Economics. However, in an interview with The Guardian in 2016, Lewinsky revealed that the scandal followed her to London, too. The first weekend she spent there, she met a woman who told her "she knew really high-powered people, and [Lewinsky] shouldn't have come to London because [she] wasn't wanted there." However, her overall experience of living in London remains a positive memory. "I loved being in London, then and now," Lewinsky admitted. "I was welcomed and accepted at LSE, by my professors and classmates."

Lewinsky mostly stayed out of the limelight at the time, and on the rare occasions she was seen publicly, the activist kept her fashion simple and sophisticated. Classic black clothing pieces were her go-to, and she often accessorized them with statement jewelry. Now in her mid-30s, fashion still played a role in her life, but it was clear that Lewinsky was exhausted from the fact that her past kept haunting her. Exploring fashion in a public space, such as attending red-carpet events, undoubtedly led to a resurgence of discussion on the '90s scandal.

Between 2009 and 2013, Monica Lewinsky completely disappeared from the public eye. While it had been over a decade since the scandal, the negativity surrounding it didn't calm down. Starting a self-care routine that actually works is crucial for self-perserverance and happiness, and it seemed as if Lewinsky needed some time off to heal herself.

While she was avoiding photographers and living her life very privately, on the rare occasions we did get to see her, it was clear that she was happier. Her skin was glowing, her hair was super shiny and healthy, and it seemed as if she had moved on from the ghosts of the past that were haunting her. In fact, Lewinsky's hair and skin were looking the best they ever had, making us wonder just what her beauty routines were at the time.

2014 marked a crucial year in Monica Lewinsky's career, as that was when her essay "Shame and Survival" was published in Vanity Fair. With it, Lewinsky and the '90s scandal were introduced to a new generation of young women who quickly realized just how the story was spun against the young government assistant. "We have created, to borrow a term from historian Nicolaus Mills, a 'culture of humiliation; that not only encourages and revels in Schadenfreude but also rewards those who humiliate others, from the ranks of the paparazzi to the gossip bloggers, the late-night comedians, and the Web 'entrepreneurs' who profit from clandestine videos," she wrote.

All of a sudden, people saw Lewinsky for what she was at the time of the scandal — a young woman who was painted as the villain of a relationship that had a multitude of imbalances from the get-go. With the published essay, more and more people became fond of the activist, who was now using her fame and her voice to shed light on issues that mattered to her. In 2014, Lewinsky attended quite a few public events, and her go-to choice for them seemed to be black dresses. Lewinsky's looks were safe and boring, but considering that she was reintroducing herself to the public that had previously destroyed her reputation, it was clear that she was cautious of how she was going to be perceived. Of course, while black dresses can seem bleak, there are easy ways to upgrade an LBD with simple accessorizing tips.

After her Vanity Fair essay put her back in the spotlight, Monica Lewinsky used the moment to become an activist against bullying. "It's all about forming habits of action," Lewinsky shared in 2015 (via ABC News). "So a little bit of kindness, a little bit of courage, a little bit of inclusion and we can really start to shift the culture and take the power out of bullying." For the Guardian in 2016, she explained that dismantling "the shame around online harassment is the first step."

With her newfound power and by reclaiming her name, Lewinsky — who was now in her early 40s — showed that fashion can play a major role in confidence. For industry events during this period, the activist often opted for a bright-red dress that ensured no one would miss her. In fact, a little red dress is the new LBD, and it's officially timeless. While Lewinsky has always been stunning, she is also living proof that fighting for your voice to be heard and finding your inner confidence are the best beauty tools, as nothing is as gorgeous as a woman who knows her worth.

At the peak of the #MeToo movement, Monica Lewinsky used her voice to speak on the importance of consent. In 2018, the docuseries "The Clinton Affair" premiered, a project in which Lewinsky herself participated. "Filming the documentary forced me to acknowledge to myself past behavior that I still regret and feel ashamed of," Lewinsky admitted in an essay for Vanity Fair that year. "There were many, many moments when I questioned not just the decision to participate, but my sanity itself ... Why did I choose to participate in this docuseries? One main reason: because I could. Throughout history, women have been traduced and silenced. Now, it's our time to tell our own stories in our own words."

While she was using her power for things that mattered, her fashion was following suit. Lewinsky, who had become a regular at the Vanity Fair Oscar Party, explored style in a new way — by playing around with textures and colors. Even though her overall aesthetic remained preppy and sophisticated, Lewinsky allowed herself to have fun with her look, proving that even the smallest changes can have a dramatic impact.

As the 2010s were coming to an end, Monica Lewinsky had an opportunity to explore producing — and she took it. The former government assistant co-produced Season 3 of "American Crime Story" which was entitled "Impeachment." The season covered the '90s scandal, and having Lewinsky as a co-producer certainly gave it a lot more credibility. 

Now with one foot in Hollywood, Lewinsky went back to a fashion choice we'd already known her for — head-to-toe black clothing. However, unlike her fashion moments in 2014, this time around Lewinsky made black intricate and fun. From mixing a variety of different materials to not being afraid of sequins, the activist proved that fashion can be explored even in one's 40s. Over the past couple of years, Lewinsky has also slowly made the transition from a very dark-brown mane to a lighter chocolate one, and the subtle addition of lightness to her hair helped soften her features, giving her a younger appearance.

While her career in the '90s had nothing to do with the entertainment industry, in the early 2020s, Monica Lewinsky decided that production was a part of the industry she was very interested in. She launched Alt Ending Productions, and in 2021, her production company signed with 20th Television. Her career was thriving, and Lewinsky ensured she used her name for projects she was passionate about.

The early 2020s also mark Lewinsky's most adventurous era when it comes to fashion. Long gone were the days where the activist only wore simple black dresses to red carpets. Instead, now she was confident enough to have fun with graphic patterns and even wear pants to events. Her style became more versatile, while still remaining authentic. Lewinsky's hair also underwent a change, with the California native rocking sun-kissed highlights — a change that helped her achieve a more effortless look.

At the age of 50 in 2024, Monica Lewinsky starred in a fashion campaign for the brand Reformation. The campaign, titled "You've Got the Power," perfectly aligned with the activist's values and style, and just like that, Lewinsky also became a fashion model. "I don't know if this will sound corny but I think a way that women can feel more empowered is by recognizing places that they may need more assistance and asking for that assistance," she told Elle in 2024. 

Speaking of turning 50, Lewinsky admitted that she was excited to enter a new decade. "I was apprehensive about turning 49, because 39 was a really sh—- year for me, and I struggled to turn 40. I ended up with a real gift: It was a year of acceptance," she explained. "I was able to accept so much about myself and my life and where I am, and so that meant coming into 50 was great." 

While attending the annual Vanity Fair Oscar Party, Lewinsky wowed us both in 2023 and 2024. Going for delicate yet glamorous dresses, she has shown that she has a keen eye for detail, and that her place on the world's biggest red carpets is absolutely well-deserved. And Lewinsky is definitely proof that everyone over 50 should have their color analysis done, as wearing the right colors and rocking the right hair makes all the difference. "I'm excited about this new decade and I'm hopeful — which, for someone with a lot of trauma, even saying that feels scary," she added in her Elle interview. 

In the mid-2020s, Monica Lewinsky is no longer just the woman who played a role in the Bill Clinton cheating scandal. Today, Lewinsky is known as someone who speaks up, fights for what she believes in, and is actively showing women of all generations that it is never too late to start over. In 2025, she launched the podcast "Reclaiming with Monica Lewinsky," and with that, she was introduced to a new audience. On the podcast, Lewinsky engages in conversations with a variety of different celebrities, always discussing just how important reclaiming is to one's existence. "These are meaningful and surprising personal conversations through the prism of reclaiming," she told The Hollywood Reporter. "Whether it's the Sisyphean task of redefining a co-opted narrative, rerecording a music catalogue to reclaim ownership, decluttering a physical space to find freedom, or even a small moment of choosing peace over escalation in a personal argument, the way people reclaim utterly fascinates me."

With this new endeavor, Lewinsky's red-carpet appearances became even more frequent, and we're definitely not complaining. She has always had a knack for making simple fashion pieces look glamorous, but in her 50s, that talent is more noticeable than ever. Sparkly ensembles and low necklines occasionally make an appearance in the activist's still-preppy wardrobe, but it is truly her contagious energy and undeniable glow that make any outfit that much better.

Speaking of women who left an impact on society, make sure to check out the 12 first lady looks that sparked fashion movements.