Chelsea Clinton Outfits That Just Didn't Work

As the only daughter of multi-millionaires Bill and Hillary Clinton, Chelsea Clinton has been in the public eye since her father became the POTUS in 1993. Back then, her fashion taste was eclectic as a 12-year-old, wearing the typical baggy '90s clothing, and she grew into her own style as an adult. Chelsea is not one to wear flashy attire or show a lot of skin and she always manages to look poised and polished, even when wearing mismatched shoes. In a January 2023 tweet, she shared, "Getting ready early this morning to head to Annapolis for ⁦@iamwesmoore⁩'s inauguration, I grabbed two black heels, and failed to grab an actual pair of shoes. I didn't notice until I was in Penn Station. ⁦@Oprah of course noticed as soon as I sat down next to her...!"

Unfortunately, that wasn't the only time Chelsea had a fashion fail. While the mom of three with Marc Mezviinsky often slays in a power suit or business-friendly midi dress, sometimes she has some misses when it comes to putting together a look. From the wrong footwear to overly pouffy dresses, the Stanford grad definitely should have thought twice before stepping out in these 'fits.

Chelsea Clinton has been an avid supporter of Pride Live Stonewall Day and has shown up at the organization's annual events in New York City. "The @clintonfoundation has long supported Pride Live and the @stonewallvisctr! For this, we are incredibly grateful and even more excited to have #ChelseaClinton be a part of #StonewallDay2023," Pride Live shared on Instagram.

While it's admirable that Clinton backs LGBTQ+ rights, her outfit for the 2023 event was a mishmash of too many different styles. The black blazer worn over her Stonewall Day t-shirt looked like something she would wear to a board meeting, while her slightly flared cropped black pants appeared to be a pair she pulled out of her eight-year-old daughter Charlotte's closet. To top it off, Clinton's chunky black moto boots lent an emo look to her bottom half, which did not match what was going on above. For a pride event, perhaps some color and a more cohesive aesthetic would have been better.

Chelsea Clinton is an avid lover of the arts and took ballet lessons at just four years old. It's no wonder she attended the Dance Theatre of Harlem's Vision Gala in 2023 dressed in what appeared to be an elongated tutu. The black Oscar de la Renta gown had a lot going on, with ribbons adorning the bodice and a full flouncy skirt that looked like it was made out of crepe paper. Perhaps she was channeling Natalie Portman's character in "Black Swan" but Clinton should have passéd on this little black dress.

Clinton must have been heeding the late designer's advice given to her years ago. "The first conversation I remember having with Oscar, I was 17 or 18, he pulled aside one evening and he said, 'Chelsea. I think I know you well enough now to ask you the following question: Why do you always look like you're trying to blend into the background?' And I said, 'Well, Oscar, because I am,'" she stated a the 2015 CFDA Awards, per Glamour. She recalled de la Renta telling her, "I think you're doing yourself a great disservice. But if you insist on wearing dark colors and standing against the wall, you should at least be dressed beautifully." Clinton definitely stood out at the 2023 Vision Gala but we think it was a bit too much dress for her frame.

The Hamptons International Film Festival isn't the dressiest of all the film festivals, especially compared to Cannes or Sundance. However, Chelsea Clinton could have shown up a little more jazzed up than a patterned green maxi dress and plain white sneakers in 2022. The author wasn't just enjoying watching some films either — she was there to show a screening of her documentary series "Gutsy," which showcases trailblazing women such as Gloria Steinem and Dr. Jane Goodall.

Although the Hamptons are associated with summer vacationers, the seaside area's film festival takes place in October, which could be why Clinton chose to be covered up. According to the East Hampton Star, folks should dress prepared for the cold and possible rain during this event. "Now may not be the best time to break out those Jimmy Choo stiletto ankle boots, no matter how cute. Save them for dinner or a party," the instructions stated. It looks like Clinton definitely heeded the publication's advice, but we think she should have put more effort into her overall look with a pair of brown booties.

Chelsea Clinton showed that she likes the more is more approach when it comes to dressing while promoting her book, "The Book of Gutsy Women," written with her mother Hillary Clinton. In a dress similar to her Hamptons International Film Festival look, Chelsea chose a long light blue dress with long sleeves for a book convention in November 2019. She again opted for sneakers — a khaki green color this time — instead of a pair of more fashion-forward shoes.

It seems Chelsea is a big fan of the boho prairie look, as she wore another dress in the same fashion in September 2022 while talking about her docu-series "Gutsy" with CBS News. During the interview, it's revealed that Hillary talks about why she always wears a pantsuit in an episode. "You know, I didn't know that story. I didn't know that story. It's like, by far and away the greatest revelation I had," Chelsea stated. Like mother, like daughter, both Clinton women definitely have their favorite go-to fashion staples and it's safe to say that Chelsea's is a billowy maxi dress with sneakers.

The annual Jazz Loft Party at the Hudson Studios in New York City is all about celebrating boogie-woogie music, which is why Chelsea Clinton's black-and-white ensemble just failed to deliver. Instead of wearing a funky 'fit for the 2015 event, the former first daughter looked ready to give out communion wafers. Clinton had on a high-collared ruffled shirt tucked into a skirt that was curiously unhemmed and her black jacket with a long white collar was positively priestly. Combined with a pair of peep-toe heels, her whole look screamed church-lady rather than ragtime-ready.

Clinton has had a stunning transformation since her White House days and has been seen in bold red dresses and cool black leather jackets. Those looks would have been much more appropriate for a jazz-centered fête than a super-conservative schoolmarm outfit. One thing's for sure, if Clinton ever runs for office, this is one attire that won't have anyone clutching their pearls.