We have a lot of women on this list, primarily because they have more fashion choices (and, therefore, more options to wear something embarrassing). Men usually just wear a dark tuxedo and call it a day.

Most Expensive Red Carpet Fails in History

But, that was not the case for veteran actor John Travolta, who wore this ensemble to the 2010 Oscars. While blue jeans and a blazer would be considered dressed for the nines at Cracker Barrel, it fell flat at the Oscars. “Jeans” and “Red Carpet” should never appear in the same sentence.

3. Jada Pinkett Smith

Event: 94th Academy Awards
Year: 2022
Est. Cost: $15,000*

Jada Pinkett Smith had quite an Oscars event in 2022, to say the least. Not only did her husband smack someone across the face in her honor (causing a headline-making controversy), but Pinkett Smith also was one of the night’s worst-dressed.

Most Expensive Red Carpet Fails in History

Chris Rock should’ve made his joke about Pinkett Smith’s overpowering emerald dress (designed by Glenn Martens for Gaultier), which Evie Magazine named one of the Oscars’ “ugliest dresses” of the night.

4. Celine Dion

Event: 71st Academy Awards
Year: 1999
Est. Cost: $5,000*

Nineties critics swarmed Celine Dion for her infamous white tuxedo, which she wore to the Oscars in 1999. Made by Dior, this ensemble was considered a gigantic fashion disaster by many. Dion topped her Dior pantsuit with Ray-Ban sunglasses (studded with diamonds, of course) and a cocked fedora just so.

Most Expensive Red Carpet Fails in History

The outfit was daring as-is, but Dion wore the blazer backward, which made the pantsuit even more of a trainwreck. Still, the singer does seem to have nine lives when it comes to her fashion choices, so this wasn’t held against her for very long.

5. Jennifer Love Hewitt

Event: MTV Video Music Awards
Year: 1998
Est. Cost: $500*

There have been a lot of badly-dressed celebrities over the years, and we might’ve forgotten about this particular look, except Jennifer Love Hewitt reposted it in 2018. The picture of her and Carson Daly brought back memories of this red carpet failure, which mixed goth and glam in an underwhelming way.

Most Expensive Red Carpet Fails in History

The actress wore a black, beaded minidress with a sheer overlay. Of course, we can’t forget to mention the glittery skin, courtesy of the ’90s need to glitterfy everything. While some people thought this look was chic, others thought it was cringe.