Monica Lewinsky's Most Talked-About Outfits

Since becoming a public figure in the late 1990s, Monica Lewinsky's fashion choices have been widely dissected and we're not surprised. After all, let's not forget that little blue dress she wore during her affair with Bill Clinton, which became a major part of the impeachment trial against him. The piece became iconic, to say the least — not that Lewinsky is thrilled about it. 

As noted by Washington Press, Lewinsky had been wearing the dress during one dalliance with the then-president, and as a result of her not dry-cleaning it right away, his DNA was on it. However, when she told her friend Linda Tripp that she was considering having it done, she was strongly advised not to. Unbeknownst to her at the time, Tripp was a Clinton whistleblower — and let's just say, she went to very harsh lengths to stop Lewinsky from removing valuable evidence. According to Time, she told her it wasn't worth re-wearing the dress, as it would make her "look fat." How very '90s. 

Ultimately, Lewinsky didn't clean the dress, and it was used as evidence against Clinton. As such, the dress has been the subject of hundreds of articles over the years. And, in 2015, reports emerged that Lewinsky had even been offered $1 million for it by Erotic Heritage Museum. However, she didn't sell — and if her 2014 comments to Vanity Fair are anything to go by, she may have gotten rid of it. 

In light of all the drama surrounding the blue dress used in the impeachment trial against Bill Clinton, it's not exactly surprising that she's tried to distance herself from it. In fact, in one appearance on "Last Week Tonight with John Oliver," she even revealed that while she'd gone as herself to one Halloween party, she'd simply worn the black beret she'd worn with the dress. "Beret things I can laugh at, other item-of-clothing jokes, not as much," she said. It kind of makes sense, then, that in 2018, she decided to debut a very different blue number.

Many will recall that 2018 saw Lewinsky attend the Vanity Fair Oscars Party in a statuesque blue dress with an asymmetrical neckline. Of course, the style was very different from the one that spawned a hundred headlines several decades prior. However, many couldn't help but point out that the choice of color seemed very intentional. After all, just more than a week before the event, Lewinsky had written an essay for Vanity Fair about how being recognized by the #MeToo movement had helped her heal from the scandal that came to define her. 

As was noted by Daily Mail, there was a sense that wearing a new blue dress may have been Lewinsky's attempt at changing the narrative, almost a rebirth in a sense. We're here for the sentiment. Plus, it doesn't hurt that she looked like a goddess in it. 

Unfortunately, not all of Monica Lewinsky's red carpet choices have been quite as well received as the blue gown she wore to the Vanity Fair Oscars Party. In 2015, she rocked a red, off-shoulder balletic dress to that year's Tony Awards. Our thoughts? It's certainly not the worst red carpet look of all time, even if the execution felt a little off. However, many fashion commentators were left seriously unimpressed. 

The Daily Mail placed Lewinsky on their worst-dressed list, labeling the look as "frumpy." Yahoo Life weighed in on it, too, poking fun at the outfit as a prom look and even commented on it being age-inappropriate. Yikes, much? 

Other than criticism of the outfit itself, it bears mentioning that many of the same outlets that slammed the ensemble shared a disclaimer that they were fans of Lewinsky herself. In addition to loving seeing the former White House intern out and about in public, they were also impressed by how she had begun using her platform for good (as many know, Lewinsky now makes a living from her advocacy against cyberbullying). Hey, the look might not have been a hit, but it certainly got people talking about her mission, and that's a win in itself! 

While not all of Monica Lewinsky's post-impeachment trial outfits have been popular, there's no denying they're consistently tied to her personal and professional advocacy for women. As such, it wasn't exactly a surprise when, in early 2024, she was named the face of Reformation's "You've Got the Power" collection. 

Of course, as a model, the outfits in the campaign aren't Lewinsky's own, per se. However, speaking to Harper's Bazaar, the chief creative officer at Reformation shared that everything was done with her in mind. "She is a bullseye for the Ref archetype — smart, funny, sexy — and a walking embodiment of what it means to embrace your power," Lauren Carin Cohan explained. Sure enough, of being part of the campaign, which was done specifically to encourage people to vote, Lewinsky told the outlet, "A Ref woman is an empowered woman — and an empowered woman uses her voice." 

Responses to the campaign were overwhelmingly positive. In fact, CNN even named the image of Lewinsky in a black dress from the line their "Look of the Week" for the final week of February. From scandalous headlines revolving around her blue dress to starring in a campaign for workwear and getting her flowers for it — we love this redemption arc!