Monica Lewinsky's Style Transformation Can't Go Unnoticed

Love her or hate her, there's no denying that Monica Lewinsky has left a permanent mark on pop culture history. Her affair with former President Bill Clinton in the '90s changed the course of her life forever. She was no longer just another young thing trying to make it in Washington, D.C., but a household name known for reasons you wouldn't want your mother to know about. Lewinsky spent years trying to carve out a future for herself in a world where she couldn't simply
go out and get a regular job anymore. Instead, she became an outspoken anti-bullying activist, a writer, a podcaster — and one of the most surprising style icons of the century. 

That's not to say that Lewinsky has always been serving looks. In fact, her early years in the limelight made us wonder why skirt suits were ever a thing, and whether '90s business style should be wiped from our collective memories entirely. But thankfully, Lewinsky's style evolved over the years to become something truly wonderful to behold, and a statement to women everywhere: You can always reclaim your narrative — and look drop-dead gorgeous while doing it. Long live Lewinsky.

Monica Lewinsky is so synonymous with one of the biggest scandals in political history that it can be difficult to remember that there was a time when she was just a sweet little girl from Beverly Hills. Lewinsky was raised in an affluent family in a home worth an impressive $1.6 million, and certainly didn't seem to want for anything in her early years. Perhaps it's hardly surprising, given her parents' impressive wealth, that photos of little Monica Lewinsky show her looking prim and proper in a sweet outfit with a white Peter Pan collar, her thick, brunette hair pulled back with a dainty ribbon. 

A '70s baby, Lewinsky was a pretty youngster with her whole life ahead of her. If she had known then that her future entanglement with the president of the United States, Bill Clinton, would bring her childhood photos to public attention, would she have opted to wear a different outfit? We've seen a lot of celebrity photos that feature embarrassing before-they-were-famous style choices, and we have to say that Lewinsky has done pretty well here. While we can't see the full picture, she looks like the embodiment of a happy, healthy, well put-together child. If only all of our childhood photos were like this! 

When news of the alleged affair between then-President of the United States Bill Clinton and his White House intern, Monica Lewinsky, broke, it created a tidal wave of political proportions. It wasn't just a Washington scandal but a pop culture phenomenon that had set gossip columns across the globe ablaze. When the public first became aware of Lewinsky, she consistently wore business-chic, very '90s outfits. Lewinsky, who has been very open about her struggles with her weight over the years, appeared to prefer to wear baggier garments with looser fits to disguise her shape. This photo, taken when she visited the offices of the FBI in 1997, shows the then-20-something in a gray skirt suit with a short hemline, sheer nude pantyhose, and white pumps. It does little for her figure — but we suspect that was the point. 

Lewinsky's hair was coiffed into a stylized blow-out that sat just above her shoulders and was ironically reminiscent of former first lady Jacqueline Kennedy Onassis. Though Lewinsky was trapped in an impossibly harrowing situation, she was always photographed looking remarkably put together. She completed this outfit with a matching gray scoop-neck blouse and a set of pearls. '90s style was a little tricky, but looking back at this now, there's no denying that this look completely ages Lewinsky, who should've been wearing much more playful, on-trend styles to suit her age. We can't help but feel her mother may have had a hand in styling her throughout this time.

As soon as the cat was out of the bag and the affair was public, we were embedded in every detail, from Monica Lewinsky's dating history to what her relationship with Linda Tripp was really like. Needless to say, photographers were keen to photograph her even when she least expected it, like when she went out for dinner in downtown Washington, D.C. in 1998. This rare, off-duty, more casual look of Lewinsky's from the time shows her wearing a dark navy dress with a white pattern. The short-sleeved number was still fairly loose, as per her style at the time, but cinched in slightly around the bust. Accessories were kept to a bare minimum with a pretty, dainty necklace and a lilac purse. 

Lewinsky wore her short, dark hair swept away from her face in a half-up, half-down style that showed off her youthful complexion. All in all, this whimsical look ticked every box for fresh '90s style — and showed that Lewinsky was just as capable of throwing together something more representative of her age than a dowdy skirt suit. We're still here for it — and for her thousand-kilowatt smile, considering everything she was going through at the time. That's the biggest style win of all.

Can we add embroidered flowers to fashion trends from the '00s that deserve to make a comeback? The turn of the millennium ushered in a ton of changes, not least in the fashion world. At that time, Monica Lewinsky was still trying to navigate a world in which she was famous for all the wrong reasons. In 1999, the former White House intern began designing handbags, turning to the internet to sell her wares before the line was picked up by Henri Bendel. For the launch, Lewinsky had a notably slimmed-down figure thanks to her recent role as spokesperson for the weight loss brand Jenny Craig, and experimented with a little more color than we'd previously seen. She matched an embroidered jacket with a pink snakeskin top to meet her fans, happily signing the bags as she went. 

Lewinsky paired her outfit with blush-pink, fresh-faced makeup for a look that screamed millennium fashion queen. Some people would've shied away from the public eye forever, but Lewinsky's fans were pleased to see her in such fine form. "Her figure's incredible," attendee Judith Violin told The New York Post. "She seems really focused." With her pale skin and dark eyes, pink is definitely Lewinsky's color, and it was a welcome departure from her typical dark or neutral palette. 

Unfortunately, Monica Lewinsky's love life hasn't gotten any better since her Bill Clinton affair, but the same can't be said for her style — and that's a blessing. In 2014, Lewinsky walked the red carpet at TrevorLIVE LA, an event for The Trevor Project, and she looked a million bucks. Her slimmed-down figure was hugged by a simple but flattering black tiered maxi dress that cascaded to her ankles. Silver pumps peeped out from underneath the material, giving the monochromatic look a much-needed pinch of shimmer. Never one to overdo it (or do much at all) in the realm of accessories, Lewinsky opted to forgo any heavy jewelry, instead pairing the look with a black clutch bag. 

Her makeup was also fairly understated, with rosy cheeks and a dose of classic black eyeliner on the upper lid. Meanwhile, her hair was looking on-point in a chic, messy half-up-half-down style that pulled the attention to her face. While we would have loved to see Lewinsky experimenting with a little more color, we can't dispute that a black dress like this is absolutely timeless — and very Monica. 2014 was a big year for Lewinsky, who had a public resurgence. In a scathing piece she wrote for Vanity Fair at the time, Lewinsky called out harmful internet behavior in a bid to help others, noting that while she had tried to keep a low profile (for a decade prior, she refused major interviews), it was simply impossible due to her notoriety. "No longer," she wrote. "It's time to burn the beret and bury the blue dress. And move forward."

Playing with color can be difficult. It can have a huge impact on everything, from the hue of our skin to how comfortable we feel. For those of us who are inclined to stick to darker colors, making a bold color statement can make us feel like a fish out of water. There's no doubt that Lewinsky likes to stick to a deeper, more muted color palette for events, so when she rolled up to the InStyle Badass Women Dinner in New York in 2019 wearing a bright red pantsuit, there's no doubt it was a departure for her — but it paid off. The perfectly tailored wide-leg pants and the stylish cut of the blazer fit the theme of the evening perfectly. 

This was power dressing at its finest. Lewinsky wore simple black pointed pumps to round off the look and wore her long hair in loose curls. At this time, Lewinsky had also experimented a little with her hair color, sticking to the dark base but adding notes of caramel to the tips to give it a little lift. At this point in her life, Lewinsky was well on her way to reclaiming her narrative. Instead of shying away from her story, she kept busy. She even won the 2025 Webby for best influencer endorsement (advertising) with her anti-bullying campaign #DefyTheName with BBDO New York. 

In 2021, Monica Lewinsky's story was told on the small screen with "Impeachment: American Crime Story." Beanie Feldstein took on the role of Lewinsky, while Sarah Paulson donned prosthetics to play the former intern's colleague-turned-fake friend and whistleblower, Linda Tripp. The show certainly made waves, not least because of Monica Lewinsky's involvement with "Impeachment." The dramatization, which Lewinsky helped produce, finally gave her the reins to tell her story in a way that she wanted to — and for the premiere, she looked like a woman in control. Lewinsky walked the suitably blue carpet in an above-the-knee skater dress with a geometric blue and red pattern. 

She complemented the flirty outfit with leopard print pumps with silver straps and topped it all off with a brilliant sun-kissed tan. Lewinsky's hair was also lighter than it had been in previous years, marking a true change from the almost-black shade she preferred in the '90s and '00s. There was something about this dress, as well as how Lewinsky carried herself, that ushered in a brand new era for the star. She was no longer there to be talked about. She was ready to confidently control the conversation — while serving red carpet looks and taking center stage. 

It's true — some photos that prove Monica Lewinsky is aging like a fine wine. This is just one of them. In 2023, Lewinsky attended the annual Vanity Fair Oscar party looking like a monochromatic dream hauled straight from the early 1900s. The Rodarte creation cinched the LA native in at the waist, the white material flowing effortlessly down to her ankles, while the detailed black lace at her neck and sleeves offered just enough drama. Lewinsky added a pop of color with bright red lipstick and big, statement earrings. This was an undeniably old Hollywood aesthetic that will (and has) stood the test of time. If there was ever any doubt that she had the style prowess to contend with the rest of Tinseltown's elite, it was well and truly put to bed with this look. 

Lewinsky kept her hair sleek in a side part, tucked neatly behind her ears to reveal her stunning cheekbones and confident smile. She may have shied away from more dramatic looks like this in the past, but Lewinsky's more recent looks, such as this one, prove that she's done living in the shadows. If only Monica from 1998 could have seen where she would eventually end up, perhaps she would've had the bravery to shelve the skirt suits a little sooner.

By the time 2025 rolled around, we were sure of one thing — Monica Lewinsky's post-Bill glow-up had reached far beyond looks. Yes, we can't deny that Lewinsky reinvented herself as something of a style goddess (which we would never have expected in the '90s), but it reached far beyond that. For the Vanity Fair Oscar Party that year, the svelte star wore a daringly sexy black Stella McCartney gown with a deep sheer V-neck. It was empowering in every sense of the word to see Lewinsky up there with the best of them, not as a former White House intern with a very public dating history, but as an activist, a writer, and a woman who knew her worth. 

This dress demonstrated that Lewinsky wasn't afraid to be seen as what she is — a multifaceted, beautiful, and powerful woman who wasn't going to blend into the background anymore. Needless to say, we were totally here for it. Her thick, glorious locks were lightened around the ends and waved in an effortlessly chic way, falling around her shoulders. As always, accessories were basically nonexistent, but do you really need any when you've got a dress this stunning? Black can definitely be boring when done one too many times, but this is a tried and true testament to "if it ain't broke, don't fix it."

What do Amanda Knox and Monica Lewinsky have in common? Both American women were at the center of highly publicized legal cases, both ended up vilified and shamed, leaving their reputations tainted forever, and both have spent years trying to set the record straight. Perhaps it's no wonder that Lewinsky showed solidarity with Knox when she executive-produced the 2025 miniseries "The Twisted Tale of Amanda Knox." For the premiere, Lewinsky looked like a glittering star who was better suited to being on the silver screen than pulling the strings behind it. She wore a stunning gold sequin blouse with a matching midi skirt that caught the light beautifully while also complementing her skin tone. 

Her nude pointed shoes were a fabulous choice, topping off the ethereal look perfectly without drawing too much attention away from the main event. Lewinsky has really fine-tuned the art of letting a great outfit speak for itself, never complicating things with garish purses or jewelry. It was a nice change to see her hair pulled up away from her face for this event because we're so used to seeing her trademark loose waves.