Chelsea Clinton is an author, philanthropist, and the daughter of Bill and Hillary Clinton.

Thank you @BuzzFeed for reminding me of my awkward yrs…" per X, formerly known asTwitter.

Clearly, plenty of folks have had opinions about Chelsea’s fashion choices over the years.

Chelsea Clinton smiling

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.

Chelsea Clinton smiling

Unfortunately, this dress was a major flop.

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.

Chelsea Clinton smiling

Yet, the worst styling offense was what seems to be an Apple Watch with a sporty band.

Clinton’s flowy boho dress clashed with the preppy, business casual nature of the blazer.

Interestingly, the worst part of this outfit is actually its squandered potential.

Chelsea Clinton smiling

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.

Chelsea Clinton smiling with her book

First off, this outfit has no extra interest or fun accents.

A little black dress is, of course, a closet staple.

Yet, this one isn’t the best go-to pick for Clinton.

Chelsea Clinton smiling

Both the sleeves and the hemline are strange lengths.

This dress is the definition of “blah.”

Its shade of taupe washes her out and makes all of her features fade to the background.

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.

The risk she took, however, was unarguably a strange one.

She sported a sparkly long-sleeve top with a deep-v cutout neckline.