The Best And Worst Outfits Cheryl Hines Has Ever Worn

When it comes to stunning transformation of Cheryl Hines, both the evolution of her career and her complicated personal life are sure to come to mind, but her style has transformed too. The "Curb Your Enthusiasm" star's red carpet looks certainly have gotten people talking, and as the wife of the United States Secretary of Health and Human Services Robert F. Kennedy Jr., she has been making fashion statements in the world of politics as well. Her direct connection to the MAHA movement has been polarizing, to say the least, but many of the gorgeous ensembles she's sported at official galas have not sparked any controversy.

While she's definitely rocked her fair share of bold and beautiful outfits over the years, it's safe to say they haven't all been winners. Of course, no one can expect perfection every time, but on several occasions, the veteran actor really missed the mark, catching people's attention in the worst way with outfits that range from inappropriate to frankly bizarre. Here are some of Cheryl Hines' most memorable fashion statements that turned heads, for better and for worse.

In January 2025, Cheryl Hines proudly stood by husband Robert F. Kennedy Jr.'s side at the presidential inauguration events. While Hines was there to support the Secretary of Health and Human Services, she didn't miss the chance to make a sartorial statement. For the Make America Healthy Again Inaugural Ball, she wore a platinum silk lamé dress designed by Romona Keveža, the same designer who made her custom wedding dress in 2014. The platinum dress was striking, but still elegant and regal. It made an impact without overstepping the mark. Definitely a win.

In addition to making cringeworthy makeup mistakes, Cheryl Hines has also made some fashion missteps over the years. Take this ruffled dress to the 10th Annual LMGI Awards, for example. Frankly, it's entirely too much. The pattern of the dress is busy, but it maybe could have worked if it did not clash with the texture. In addition to an intense floral pattern, the puffy sleeves, high neck, and the four-tier skirt make it too overwhelming. Critics and fans alike seem to agree that it was one of Cheryl Hines' many questionable fashion choices.

Cheryl Hines is the epitome of grace in this ensemble. She wore a classic "little black dress" to the "A Bad Moms Christmas" premiere in 2017, but it wasn't just any old black dress. This one has a deep yet classy neckline, and it accentuates her figure in an elegant and sexy way. The velvet of the fabric adds a layer of propriety, making it a perfect dress for a premiere, a gala, a dinner, truly any occasion. Pairing it with silver dangling earrings gave it the final touch.

No one can deny this is quite the statement, but it might have crossed the line. In 2006, the actor wore this spectacular gown for the 58th Annual Primetime Emmy Awards. As readers can see in the photo, she chose a shiny purple satin dress. That alone was a bold choice, but what pushed it over the line is the faux backless detail, with an intricate beaded panel of illusion netting, which she combined with heavy golden jewelry and earrings. In a 2020 chat with People, the actor reflected on the negative buzz her dress generated with a laugh. "Somehow, I was on the worst and the best dressed list," she said. "It had flesh-colored netting on the back with beads. It reminded some people of an ice-skating costume. They had strong feelings about it."

For the Season 12 premiere of "Curb Your Enthusiasm," Cheryl Hines went for a classic look with a twist. She wore a floor-length strapless dress, and the bright red was definitely eye-catching without being too much. It was form-fitting, but not inappropriate, and the asymmetrical ruching of the fabric gives it a relaxed touch without taking away from the glamorous vibe. She paired it with beautiful, chunky gold earrings that complemented the outfit without stealing the show.

Where to begin with this one? Cheryl Hines' outfit choice for the "How To Lose a Guy in 10 Days" was... definitely a choice. In her defense, it was 2003, and weird style moves were being made left and right in the Y2K era. Dare we say this look manages to be too much even for the time period. She attempted to combine two prints that seem to hate each other: the leopard print of her skirt and the sheer lace of her top. At least she kept both pieces in the same color scheme. But still, this is definitely a misstep. It's too busy, the ruffles of the lacy top don't match the seemingly heavy fabric of her skirt, and it's overall overwhelming to look at.

Yet another "little black dress" with a twist, and another absolute win. Cheryl Hines and her husband, Robert F. Kennedy Jr., attended the opening night of "Les Misérables" at The Kennedy Center in 2025, and she was the image of grace and elegance. She wore a black bodice strapless dress with a beautiful feathered fringe at the hem that makes it into an original look without losing the timeless elegance of a long black dress. The feathered hem gives it movement and glamour, giving a modern touch to a classic look. She wore understated black heels, and gave the outfit a finishing touch with a crystal-embellished black clutch.

This outfit could have been a win if it wasn't for the length. For PETA's 30th Anniversary Gala and Humanitarian Awards, Cheryl Hines chose a mini dress with a geometric gray and white pattern that is, as far as we're concerned, too shiny. The straps are thin and look like beads. If she had worn this on a night out or a birthday party, it would have been a great choice. But this kind of outfit feels a little too casual for the occasion. She combined it with silver strappy heels and a small metallic clutch that matched them perfectly. A cute outfit, just not the most appropriate for the event.