Cheryl Hines Outfits That Had People Talking For All The Wrong Reasons

Long before Cheryl Hines married Robert F. Kennedy Jr., she was known for her role as Larry David's wife on HBO's "Curb Your Enthusiasm." In fact, it was David who introduced Hines to Kennedy in 2011, which led to the couple getting engaged in April 2014. Despite the fact that Kennedy, who's now the U.S. Secretary of Health and Human Services, had already discovered a parasite had eaten some of his brain in 2010, he actually had initial reservations about dating an actress — as if that could possibly be worse than having a brain worm. Because of this, he turned to David for advice. According to The New York Times, David said of Hines, "She's the most solid person I've ever met... Nothing you ever do will rattle her." As more information has come out about Kennedy and his wild conspiracy theories, it turns out that David was absolutely right about Hines.

Although Hines and Kennedy's marriage has some glaring red flags we just can't ignore, it's worth noting that they've both made some questionable choices. While Hines has never dumped a six-month-old bear cub in Central Park, she has worn some outfits that had people talking for all the wrong reasons — suggesting that maybe both she and Kennedy are a little delulu. From being underdressed, to overdressed, to simply missing the mark, Hines has had more than her fair share of fashion faux pas.

While there's nothing really wrong with this dress, per se (although a bolder color would be far more complementary on Cheryl Hines), it just doesn't seem appropriate for the UCP of Central Florida Gala. As Hines wrote in the Instagram caption that accompanied this photo, the gala celebrated the organization for "creating community and opportunity for children to reach their potential... Always an honor to share the night with these amazing families, supporters, and teachers." That being said, as a family event, one would think Hines would have chosen a dress that didn't highlight her undergarments. While exposed bras have made a comeback, this wasn't the place for it.

For the 2022 Emmy Awards, Cheryl Hines opted for this full-length dress that really misses the mark. For starters, the print makes it too casual for the event; and the neckline, although fun, isn't exactly the best route to take for the Emmys. If Hines had worn this to a club or to dinner with RFK Jr., then it would have made sense. Although Hines didn't make our list of the Emmy Award dresses that were total fashion disasters, this gown would have, if the list had been a little longer.

In November 2020, Cheryl Hines posted this photo on Instagram of her dressed to the nines while holding a very large American flag. In the caption, Hines wrote, "Congratulations to #JoeBiden #KamalaHarris History has just been made!!! Our first female Vice President!!! Looking forward to our new First Lady Dr Jill Biden!" While it's great to see her supporting democratic politicians, especially considering where she'll find herself on Inauguration Day in 2025, she just seems a little too dressed up for the occasion — especially since it looks like she's standing in a driveway. Also, not to nitpick, but the colors in the dress and the colors in the flag are really clashing.

Leopard print can go in one of two directions. It can look timeless and sophisticated, or it can look tacky, serving up major mob wife aesthetics. Unfortunately for Cheryl Hines, she's in the latter category. Because of the design of the shirt and the pants that appear to possibly be leather, it looks more gaudy than anything else. While the only context for this photo is Hines mentioning that her dog is her favorite accessory, between the outfit and the pose, it makes one wonder if Hines is hoping to get cast as Angela Norris' sister on "Landman."

Although Cheryl Hines made a name for herself thanks to "Curb Your Enthusiasm," she remains mostly a character actor outside of that series. That being said, she's probably not getting the same caliber of invitations as, say, Nicole Kidman; so when Hines does show up to an event, you'd think she'd make more of an effort. For the 10th Annual LMGI Awards in August 2023, Hines wore this dress that leaves more question than answers: Why this print? Why long sleeves in August? Was there a ruffle competition happening after the ceremony? This overly-busy dress isn't doing her justice.

If you know anything about Fashion Week, then you also know that this is definitely not an expected look. Granted, this photo of Cheryl Hines is from 2005; but even back then, it's an underwhelming dress to wear to such a fashionable event. While there's a chance that Hines is wearing a dress from designer Sue Wong, whose show she is attending, she could have gone for a more elevated look. Instead, between the dress and average sandals, Hines looks like she's heading to a garden party and not the front row of a fashion show.

For the 2003 premiere of "How to Lose a Guy in 10 Days," Cheryl Hines tried to pull off the mixed print trend and epically failed. Between the red and white leopard print skirt, the sheer pink polka dot top, and the light brown and white sandals, it's a good thing Hines wasn't in the film. Joan Rivers definitely would have dragged her for this outfit. What makes these choices even more perplexing is that none of them even fall into the category of Y2K fashion trends. If they had, that would make for a great argument or explanation — but everything about this ensemble is coming out of left field.

When Cheryl Hines attended the 2006 Emmys in this dress, chatter followed almost immediately. "Somehow, I was on the worst and the best dressed list," Hines told People in October 2020, referring to the purple Georges Chakra dress with a beaded design on its flesh-colored netting back. "It reminded some people of an ice-skating costume." While not as casual as some of her other Emmy looks, it definitely wasn't a winning outfit at all. It wasn't just that there was a figure skating vibe to it, but it looked cheap too — something that never goes over well at awards ceremonies.

For the HBO Post Golden Globe Party in 2018, Cheryl Hines decided to go with this dress that looked like she let a small child scrawl on the bust of it. Although the black sequin bodice and sheer top would have been elegant and simple, the white scribbling along the neckline takes away from the entire ensemble. Some of that has to do with the vast contrast between black and white — for example, a deep burgundy instead of white would have worked better. But it could also be the design itself and the fact that chicken-like scratches on any dress looks messy.