Megyn Kelly's Most Inappropriate Outfits Yet

Journalist and pundit Megyn Kelly is a polarizing figure, but if there's one thing everyone can agree on, it's that the former Fox News anchor isn't afraid to take big swings. Kelly has put her foot in her mouth on air more than once. However, she's always found a way to bounce back and somehow keep her career afloat, whether making the move from Fox to NBC or parlaying her subsequent booting from that network into her independent podcast, "The Megyn Kelly Show." Her many gaffes and controversies haven't always been verbal, either — throughout her stint in the public eye, Kelly has also drawn a lot of criticism for her fashion choices.

Many people — and women, in particular — are subject to sartorial scrutiny when in positions of power. For instance, the public is quick to point out inappropriate royal outfits we'll never forget or controversial outfits worn by the presidential family. Because journalists often travel in the same circles, traversing both political and professional arenas, figures like Megyn Kelly are held to similar standards. Unfortunately for Kelly, however, her fashion sense hasn't always hit the mark. From dresses dubbed too revealing to Halloween costumes that flopped dramatically, Megyn Kelly has repeatedly provoked scorn for her inappropriate styling.

Megyn Kelly probably had plenty of insightful observations to make as she reported on the 2016 Republican National Convention. Sadly, viewers were completely distracted by her shoulder-baring dress choice. "Hard to take your coverage seriously when @megynkelly looks like she's working for an escort agency," said one user on X, formerly known as Twitter. Yikes. Another X user seconded, "It's like @megynkelly forgot to finish getting dressed." Kelly has since clapped back at critics of this look, telling The New York Times, "I can be smart and challenging while I wear spaghetti straps, and everyone is just going to have to get their heads around that."

Think what you like about Megyn Kelly, but the woman is a sharp dresser. Offered the chance to attend the 2017 Met Gala, her dress was typically attractive — but we're not so sure it fit the event theme, which celebrated avant-garde Comme des Garçons designer Rei Kawakubo. Kelly's red gown, which featured floral embroidery, pearl embellishments, and a black sash, would have worked on many a red carpet but failed to capture Kawakubo's philosophy of tension and duality. Was it one of the worst outfits in Met Gala history? No. Interestingly enough, though, Kelly hasn't been back to the event since and even called the Met Gala "trashy" on "The Megyn Kelly Show" (via YouTube). Sour grapes, much?

Megyn Kelly struggles with Halloween — as evidenced by her reputation-destroying questions surrounding blackface, which was one of the biggest scandals to ever hit morning TV. Even Kelly's earnest attempts at a fun costume seem to go over like a lead balloon, such as her 2017 Shania Twain 'fit. Kelly dressed up as the "You're Still the One" singer while co-hosting "The Today Show" and joking, "Every shred of my dignity is gone" (via YouTube). Unfortunately, viewers seemed to agree. "Watching @megynkelly grasping at legitimacy and embarrassing herself ... Is this a race to the bottom?" asked one user on X. Another X user added, "Celebrating Halloween with some scary viewing: Megyn Kelly on the Today Show. Cringing along."

Megyn Kelly unintentionally caused another stir in 2017 when she got caught chatting with high-profile figures like Russian leader Vladimir Putin and Indian Prime Minister Narendra Modi while wearing a shoulder-baring and figure-hugging velvet cocktail dress. Originally retailing for $990, you can now find the Yigal Azrouël piece on eBay for closer to $135 — but its price was never the issue. "Disappointed that Megyn Kelly chose this dress to meet with Putin," commented one user on Houzz, while another called it "ridiculous and unprofessional." 

At state dinner party at Konstantin Palace in St. Petersburg with Russian President Putin and Indian PM Modi. More tonight @NBCNightlyNews pic.twitter.com/FX5kjfIJAf

— Megyn Kelly (@megynkelly) June 1, 2017

However, it's worth noting that this was not the real interview — it was, in fact, a dinner party for the dignitaries to mix and mingle. Was Kelly's dress still a shade too provocative for a gathering of world leaders? Perhaps. But at least her official interview ensemble was more restrained.

We'll say one thing for Megyn Kelly: She doesn't bow to external fashion pressure. While her spaghetti straps and velvet cocktail dress raised eyebrows, past backlash didn't sway her decision to wear a black leather mini kilt to interview Donald Trump in 2023 — or to share a photo of the meeting online. Alas, audiences were quick to blanket the pundit with newly scathing commentary. "You forgot your whip," one user wrote in the comments of Kelly's own Instagram post. "What the hell is she wearing? Needs to cover those legs," added another.

Megyn Kelly's Halloween struggles struck again in 2024. After Joe Biden called Donald Trump's supporters "garbage," Megyn Kelly decided to poke fun at the insult through her spooky season costume. The journalist donned a belted trash-bag poncho over black leggings, then topped the makeshift ensemble with a bright red MAGA hat. It may not have ranked among the worst celebrity Halloween costumes of 2024, but Kelly's politically charged pun invited criticism from many onlookers. "Nailed it, hon. Weekly pick-up is Tuesday. Be at the curb," commented one Reddit user. Another added, "White trash Barbie." And one user on X sharply quipped, "Dressing up as yourself kind of defeats the purpose of Halloween."