Monica Lewinsky Photos That Prove She's Aging Like Fine Wine (Sorry, Hillary)

It's been decades since Monica Lewinsky's life was forever altered by her nearly two-year-long affair with Former President Bill Clinton, which was exposed to the world in 1998. The former White House intern's life following the Clinton scandal was filled with tragedies, predominantly due to the brutal shaming and harsh scrutiny she received from the public and press alike in the years that followed. Not only did Lewinsky struggle with her mental health, but she also racked up a staggering amount of legal debt, resulting in her being in dire financial straits for a while. While the affair ultimately did not end up breaking Bill and his wife Hillary Clinton's marriage, the hurt and devastation it caused to their respective families and loved ones have become Lewinsky's greatest regret in life. 

Fortunately, by age 50, Lewinsky felt like she'd finally got her long-awaited redemption arc. "It's a long journey from '98. [...] I'm grateful. I'm really grateful for where things are now," she remarked during a 2023 "Today" show appearance. A major part of the reason her 40s were "the best decade for [her]" thus far was that the former White House intern finally got to participate in telling her own story as a hands-on producer on "Impeachment: American Crime Story" (in which Lewinsky is played by Beanie Feldstein) and, thankfully, the response from younger viewers was sympathetic. "I was so overwhelmed with gratitude in that people see me for my true self now; that I have been able to find a purpose to my past; that my narrative has been revisited, and I was able to reclaim it, in large part from younger generations," she shared. But Lewinsky hasn't just been thriving in terms of her career — time has been incredibly kind when it comes to her appearance too. 

Monica Lewinsky was one of the high-profile winners at the 2019 Webby Awards alongside the likes of Will Smith, Childish Gambino, and Jimmy Fallon after she took home the trophy for the best influencer endorsement for her anti-bullying campaign, #DefyTheName. Before receiving her award at the New York City ceremony, the then-45-year-old activist turned heads on the red carpet with her ageless appearance and luminously clear skin, which had us frantically googling the activist's beauty routine. Lewinsky, unfortunately, hasn't revealed her skincare secrets just yet, but whatever they are, they're clearly working.

Monica Lewinsky has admitted to having confidence issues when it comes to her body, as a result of years of being fat-shamed on the internet, late-night shows, and more. When asked by Vanity Fair in 2021 what she "dislike[d] most about [her] appearance," the former White House intern sadly responded, "I'm jiggly." However, Lewinsky confidently embraced her curves and showed off major cleavage in a red-hot look for the magazine's 2022 Oscars afterparty in Beverly Hills. And not even her unfortunate bangs could distract us from the super healthy, lit-from-within glow she was sporting at the event.

In December 2022, Monica Lewinsky shared a photo of herself enjoying some cookies and a coffee at the celebrity hotspot Polo Lounge, which is located inside the iconic Beverly Hills Hotel. She kept it casual for the relaxed outing, wearing a black sweater, jeans, hoop earrings, and, crucially, minimal makeup. "Bottoms up! (in my fave [Bella Freud] sweater!)," she captioned the Instagram post of her pointing at her cup of coffee, which also notably featured what appeared to be an impressive latte art depiction of herself (though it didn't look as good as the real thing!). 

Monica Lewinsky, who impressively obtained a masters in social psychology from the London School of Economics following the Bill Clinton scandal, returned to the city in February 2023 to grace the premiere of the Lily James rom-com "What's Love Got to Do with It?" in a cropped sequined jacket and black flared slacks that showed off her figure. But while her eye-catching jacket certainly sparkled under the bright lights, the main highlights of her look were actually her smile and age-defying appearance.

Just weeks after Taylor Swift's "Eras Tour" kicked off in 2023, Monica Lewinsky channeled the pop superstar in a selfie with a sleek red lip and red outfit combo. After sharing the snap on Instagram, the activist asked her followers if it was "too matchy-matchy," to which one person replied, "No, [it's] absolutely perfect!!" And we definitely have to agree. Though it's unknown if Lewinsky was actually inspired by Swift, the Vanity Fair contributing editor proved the "Anti-Hero" hitmaker wasn't the only one who could pull off red-on-red.

Monica Lewinsky proved it's never too late to make your debut as a fashion model when she became the face of a Reformation campaign in February 2024. The then-50-year-old rocked various looks from the fashion brand's workwear collection, including a cream suit and black belted midi dress, while urging people to vote in the 2024 presidential elections. In an Instagram post, she gushed that taking part in the campaign had been "the highlight of [her] year" but "was so far outside [her] comfort zone." However, we couldn't really tell from the photos since she looked like she'd been doing it for years.

The annual Vanity Fair Oscars party marks one of the few times a year you'll see Monica Lewinsky in a gown with full glam on the red carpet, so she doesn't usually go wrong with her outfit choices and makeup. However, she's never looked better than she did at the 2024 bash, where the former White House intern exuded elegance and sophistication in a strapless LBD, with a matching pair of black pumps and a clutch. She kept both her jewelry and hair equally simple, letting her stunning face and figure do the heavy lifting.

After casting her ballot early for the November 2024 presidential elections, Monica Lewinsky encouraged her followers to do the same by posting a gorgeous selfie on both Instagram and X, formerly known as Twitter. "The power is in your hands," she captioned the pic on Instagram. "Every vote counts." The activist shared more details on X, revealing that Kamala Harris got her vote. In the selfie, a beaming Lewinsky appeared to be barefaced or at least have little makeup on and sported an "I voted" sticker and a sweater with the message "You've got the power" from her Reformation collab.

Monica Lewinsky took to Instagram in February 2025 to share a gorgeous black-and-white shot of herself from a Rolling Stone interview, during which she discussed her new podcast, "Reclaiming." Regardless of whether it's thanks to contouring or not, her cheekbones and jawline looked extra sharp as she posed on the sand for the photoshoot. A few days after the post, Lewinsky kicked off her podcast with an episode discussing "how she found the strength to take back her story after the scandal that turned her life upside down."

Monica Lewinsky looked decades younger when she attended the 2025 Vanity Fair Oscars party. The 51-year-old stunned in a black Stella McCartney dress with a plunging neckline that was kept from being too revealing by a chic sheer mesh panel. She wore no jewelry except earrings and rings and let her straight brown-blonde hair flow over her shoulders. Photos of her look that the former White House staffer shared on Instagram unsurprisingly received tons of praise from her followers. "Stunning! You outdid yourself this year," journalist Elise Jordan commented, while another user wrote, "You are radiant."

In April 2025, Monica Lewinsky made a rare red carpet appearance while attending the star-studded opening night of George Clooney's "Good Night, and Good Luck" on Broadway. While her off-the-shoulder dress wasn't among the podcaster's best black tie outfits (the asymmetrical ruffled hemline was wholly unnecessary), she looked gorgeous nonetheless, sporting soft glam makeup and a half-up, half-down hairdo. She was joined at New York City's Winter Garden Theatre by a long list of celebrities, who included Jennifer Lopez, Hugh Jackman, Uma Thurman, Pierce Brosnan, and Jim Parsons, but Lewinsky managed to hold her own thanks, once again, to that ageless glow.

Shortly after her Broadway outing, Monica Lewinsky surprisingly made another high-profile appearance by joining A-listers such as Sydney Sweeney at the 2025 Hollywood Beauty Awards, which honored "makeup artists, hair stylists, stylists, photographers, and more who create the looks and set the trends with their creations for the red carpet, editorial, campaigns; as well as for film, TV and music." Though her bouffant hairdo seemed outdated compared to her recent sleeker hairstyles, she nailed the rest of the look, from the soft glam makeup to her red pantsuit and pumps. Evidently, her 40s were just the beginning since Lewinsky just keeps getting better with time.