Cheryl Hines' Fashion Choices Prove RFK Jr. Isn't The Only One Making Questionable Decisions

What happens when Hollywood meets the White House? All kinds of things, including questionable fashion choices and questionable opinions. Such is the case with actor Cheryl Hines, who married into the Kennedy political dynasty when she said "I do" to Robert F. Kennedy Jr.. After two years of dating, the couple was engaged in May 2014 and exchanged vows at the famous Kennedy compound in Massachusetts just months later in August. 

Although there have been red flags in Hines and RFK Jr.'s relationship, the couple was still going strong leading into 2025. Hines attended her husband's swearing-in as Secretary of the U.S. Department of Health and Human Services in February, a position he was hand-picked for by President Donald Trump. She also supported him when he threw his hat into the ring to become president of the United States in early 2023. 

While her husband was campaigning, Hines appeared on an episode of the podcast "Literally! with Rob Lowe," where the two discussed her potential role as first lady, should Kennedy win the election. However, rather than dishing about politics, the two actors chatted about fashion. "What if I became the first lady and every time I walked out of my room I was in a different outfit, and it was designer head to toe?  And I was just like, 'Hello, I'm here,'" she joked with Lowe. "I'll sleep in my ratty pajamas, but when I walk out in the main living area, I'll put on my Armani silk pajamas and prance around." Given some of her fashion choices over the years, the ratty pajamas may have been preferable.

Cheryl Hines hit the red carpet in March 2017 with her husband Robert F. Kennedy Jr., in the days before he officially began overtaking Trump's embarrassing trademark tan. The couple were on hand for the New York premiere of Hines' movie "Wilson." He was dressed in a gray suit with a skinny tie, while she was dressed like a contestant on "Dancing With the Stars," specifically one of the Latin ballroom episodes. 

The actor, who was also starring in the Fox comedy show "Son of Zorn" at the time, wore a bright red dress with matching high heels. The dress skimmed over her frame, ending in a fat ruffle that slid downward on an angle from the top of one thigh, all the way to her shin on the other side. The three-quarter sleeves also ended in ruffles. The combination of the bold color, the ruffles, and the shoes brought to mind an outfit that might be worn while dancing the rumba or the samba, or perhaps had she added a fruit-filled headdress, promoting the deliciousness of bananas.

RFK Jr. has provoked controversy with some of his opinions about vaccines and health matters, has caused havoc with his past drug use, and sparked rumors of extra-marital affairs, but his wardrobe choice was a far better decision than the one Hines made when picking out her outfit for the big event.

Busy, busy, busy — and we're not referring to the schedule Cheryl Hines was keeping when she attended the LMGI Awards in Santa Monica, CA, in August 2023. While showing her support for the Location Managers Guild, she turned up on the red carpet looking even more fussy than the backdrop of a thousand logos that stood behind her. 

Her dress was an overly sweet confection of multi-layered ruffles around the bottom (four — there were four layers of ruffles), that were matched by ruffles on the sleeves. The high neck of the gown led to puffy sleeves even Anne of Green Gables would admire, and the top half of the dress was defined by a sash that ran around her waist, ending in what we hoped (but couldn't verify) was not a bow in the back. The sheer fabric was a pattern of blue and purple flowers, underlined by a white slip in the name of modesty. 

As if the dress itself wasn't overdone with too many elements, Hines added a black handbag that in no way fit in with the rest of her outfit, but would have been quite appropriate had she also been giving medical check-ups to the other show attendees. We're not convinced there wasn't a stethoscope in there.

As co-creator of the Hines + Young skincare line (daughter Cat is the Young part), Cheryl Hines has been out and about promoting the products. While in Los Angeles in June 2024, she was spotted at an outdoor market showing off the line's goodies. It's a relief she wasn't trying to sell the public on fashion because her outfit was a fail from the waist down.

Attempting a casual vibe, the star donned a white blouse and navy-blue blazer, a cool and chic combo. But then she paired them with a pair of white cargo pants that were way too big for her small frame, leading us to ask if she accidentally pulled them from her hubby Robert F. Kennedy Jr.'s side of the closet. Not only were they baggy all over, but they were inches too long, causing a bunch up around her ankles. 

Making it even worse were her shoes, some sort of sneaker loafer with a rubber wedge heel. We understand being comfortable while you're on your feet all day, but the elevated heel wasn't even enough to make the pants fit better and served only to look as if she borrowed them from a nurse's closet after she raided RFK Jr.'s. It would have been better if the too-long pants covered them up even more.

Cheryl Hines may still be reading scripts, but being RFK Jr's wife has led to the star reportedly facing major consequences from his MAGA lifestyle in the form of less on-screen gigs. But before all that happened, way back in 2006, Cheryl Hines had a successful career as a Hollywood actor, and was mostly known for her role as Cheryl David on HBO's hit series "Curb Your Enthusiasm." It involved showing up to big events like the Primetime Emmy Awards, dressed to the nines for the red carpet.

For the 58th Emmys, for which Hines was nominated for Outstanding Supporting Actress in a Comedy Series for her "Curb" role, the star stunned in a deep-purple gown with shirring and a ruffled train — but not necessarily in a good way. The top back of the dress was made of sheer netting decorated with a design of sparkly gems. The dress caused a bit of a commotion, with folks both loving and hating it. "Somehow, I was on the worst- and the best-dressed list," she shared with People in 2020, over a decade after the night. 

Hines recalled the haters' reaction, noting, "It reminded some people of an ice-skating costume. They had strong feelings about it." While a twirling figure skater wasn't the first vision that popped up on our radar, once the "Bad Moms" star said it, we couldn't unsee it.

Is she a Hollywood actor? Is she a politician's wife in Washington D.C.? When you can't choose which role you want to be for one night, just be both. At least, that's what Cheryl Hines seems to have decided when she stepped out to attend the Moms Mamarazzi event and a screening of "A Bad Moms Christmas" in November 2017. Even though she went with a classic, all-black ensemble, and her pants were simple and chic, her blouse screamed multiple personalities.

Baring one smooth shoulder seemed to satisfy the need to be a showy Los Angeles star, especially when paired with a sheer, see-through fabric. But then, the conservative, ready for the White House side showed up in the form of one sleeve long enough to cover even the knuckles of her hand. That attached silk scarf tied into a perfect bow on one side of her neck? It's the Hollywood version of a conservative businesswoman (see Melanie Griffith's character in "Working Girl").

In early 2017, Hines' husband Robert F. Kennedy Jr. was already orbiting in Donald Trump's circle, with the president considering him for a potential leadership position for a commission about vaccines. Although that never came to fruition, it was evident that the Trumps and RFK Jr. were forming a political relationship, and would possibly be seeing more of each other. As it turns out, it was a good idea that Hines was already starting to build part of her politician's wife's wardrobe.