Chelsea Clinton Outfits That Missed The Mark

Chelsea Clinton is an author, philanthropist, and the daughter of Bill and Hillary Clinton. While her dad was the president of the United States, Chelsea lived in the White House from the ages of 12 to 18. It's easy to imagine just how many bad outfits most of us had during that time in our lives. Chelsea was no exception to this, and over the years, she's gotten more than her fair share of flak for her fashion sense. She even inspired a 2013 BuzzFeed News article titled, "Chelsea Clinton Was The Most Adorkable First Daughter Ever," about which she tweeted, "Happy 4th of July! Thank you @BuzzFeed for reminding me of my awkward yrs..." per X, formerly known as Twitter. 

Clearly, plenty of folks have had opinions about Chelsea's fashion choices over the years. It's only fair that whoever didn't wear some exceedingly embarrassing ensembles as teens cast the first stone, so we're focusing on Chelsea's style evolution as an adult. Needless to say, Chelsea's fashion choices have grown and changed, and these days, her style is much more refined and focused. She doesn't take many fashion risks, instead sticking to classic looks. Still, despite overall making good style choices, a few outfits have fallen flat. These are Chelsea's top five style blunders.

In April 2023, Chelsea Clinton walked the Annual Vision Gala red carpet at New York City Center. At 43 years old, the writer had made strides toward mastering her style and making fewer and fewer fashion errors by the time she hit this red carpet. Unfortunately, this dress was a major flop. The black Oscar de la Renta frock looked like a crumpled up trash bag at first glance, but further inspection only made it worse. The combination of a dropped waist and mid-calf hemline threw off Clinton's proportions, and the voluminous skirt added to the strange shape.

Clinton could have pulled off this dress with better styling by treating it like a more artistic garment. A strappy sandal, high ponytail, and statement lip would have put a different twist on the dress. With her chosen styling, though, the dress could have been swapped out for one of her mom's famous pantsuits, and it actually would have looked more congruous. Clinton's long, blown-out hair, simple makeup, and nude, closed-toe heels all clashed with the youthful, fun energy the dress could've had. Yet, the worst styling offense was what appears to be an Apple Watch with a sporty band. Many of us can relate to Clinton's apparent desire to get her steps in, and red carpet steps are steps, nonetheless. Still, it may have been better to leave this accessory in her purse for the occasion, or at the very least, switch the band with something more elevated. 

In 2022, Chelsea Clinton hit the New York City streets in an outfit that quite simply made no sense. If the star was simply photographed going for a walk in this ensemble, it would only be fair to give her a pass for its mismatched look. Unfortunately, she was en route to "The Kelly Clarkson Show" to promote her and her mom's Apple TV+ series, "Gutsy." Clinton's flowy boho dress clashed with the preppy, business casual nature of the blazer. Beyond the styles, the color palette didn't work either, making it look like it was simply too chilly to wear her maxi dress, so she grabbed whatever jacket she had closest to the door.

Interestingly, the worst part of this outfit is actually its squandered potential. From the look of it, the dress at the outfit's core has a stunning print and color palette and beautiful movement. With something different layered on top that worked better with this pretty, boho feel, this 'fit would have been a major hit. By the same token, a white tank under this jacket paired with some dark jeans or printed pants would have made for another nice ensemble for a daytime talk show appearance. Last but not least, while it may not be as glaringly clashing as it was on the red carpet, Clinton once again sported her smartwatch, which just doesn't go with the rest of the 'fit's already mismatched vibes. 

Most of us don't want to stand out every time we go to an event. Sometimes, we all just want to wear something comfortable and easy while still looking appropriate. It seems like this was Chelsea Clinton's goal when she arrived at the Beloved Community Awards in 2024. Unfortunately, this just wasn't her best look for a few reasons. First off, this outfit has no extra interest or fun accents. It's very much a plain, black dress, and Clinton didn't attempt to add any pops of color or special details with her styling.

A little black dress is, of course, a closet staple. Yet, this one isn't the best go-to pick for Clinton. Both the sleeves and the hemline are strange lengths. Paired with the high neckline and baggy fit, this dress swallows Clinton up, and she looks overwhelmed by all the fabric. A more tailored option would work better if she's looking for a simple, black dress she can pull any time she needs something easy to wear. 

In 2018, Chelsea Clinton attended a signing for her children's book, "She Persisted Around the World." While the book at the center of the event earned rave reviews, the outfit Clinton sported surely did not. This dress is the definition of "blah." Its shade of taupe washes her out and makes all of her features fade to the background. Furthermore, the dress' shape doesn't add any interest, with an awkward length of hemline and a boring neckline.

Beyond the dress' lack of details, Clinton didn't add any with accessories. She wore minimal jewelry and plain, nude flats, and kept her hair simple and straight. Adding some interest with accessories would have helped this look. Yet, an entirely different outfit would have been better; it would've been nice to see her in a bold color that complemented her natural color palette and coordinated with the vibrant colors on her book cover.

While it's best not to dwell too much on the fashion mishaps of anyone's youth, Chelsea Clinton did have one style disaster in the early aughts that was so memorable, it must be revisited. In October 2002, the former first daughter attended the launch of the Versace Retrospective Exhibition at The Victoria and Albert Museum in London wearing a truly confusing ensemble. The event was, of course, all about high fashion and artistic style choices, so it's easy to imagine why Clinton chose to take a fashion risk at an event like this one. The risk she took, however, was unarguably a strange one. She sported a sparkly long-sleeve top with a deep-v cutout neckline. She paired the top with plain, wide-legged black pants and accessorized with open-toed shoes, layered gold belts, and a sleek bob.

Clinton's worst style choices over the years usually err on the side of too boring or "blah," rather than too over-the-top and complex, and for this reason, this look stood out. It's difficult to imagine what prompted Clinton to pair all of these elements together, but it's clear she was aiming to think outside the box. While not every bold fashion risk pays off, taking them can help you expand your style and have more fun. Still, fashion risks that flopped like this one are likely what prompted Clinton to stick with simpler ensembles in the future.