Sarah Jessica Parker’s Style Transformation Proves Fashion Doesn’t Stop Being Fun Over 50

While there are plenty of fashionable ladies in Hollywood, an on-and-off screen legend that instantly comes to mind is Sarah Jessica Parker. On the HBO cult classic “Sex and the City,” Carrie Bradshaw pioneered numerous fashion and beauty trends, and in real life, Parker has been ahead of the fashion game since her breakthrough. Back in 2000, Sarah Jessica Parker gave us a dance recital look at the Emmys that may have been inappropriate, but it was undeniably fun. And in her 50s, the actor continued showcasing that, above all, having fun with fashion is what it’s all about.

While Sarah Jessica Parker had plenty of best style moments in her 50s, which spanned from March 25, 2015, to March 25, 2025, the star has also given us countless fun fashion looks. Not all of them were necessarily the best fashion choices of the decade, but they were fun, daring, and unexpected. From bright colors to unusual silhouettes, these looks are some of the most fun ones Sarah Jessica Parker gave us throughout her 50s!

In April 2015, Sarah Jessica Parker attended the launch of an SJP pop-up in Las Vegas, Nevada, a fashion collaboration between the star and Zappos Couture. The Hollywood star paired a snakeskin-print pantsuit with a black-and-yellow lace top, proving that mixing patterns can look chic and fun. In fact, the then-50-year-old actor didn’t end it there, adding even heels with a print to the look. While some might not be a fan of the mismatched vibes, the truth is that the fashion trend makes outfits more interesting.

The annual Met Gala is fashion’s biggest night, and so the star-studded event always provides a chance to have fun with style. In 2015, the gala’s theme was “China: Through the Looking Glass,” and Sarah Jessica Parker delivered with a dress she designed with H&M, paired with a dramatic headpiece by Philip Treacy. Whether you loved the look or hated it, there is no denying that the “Hocus Pocus” star’s appearance was campy and fun.

In September 2017, Sarah Jessica Parker went to New York City Ballet’s Fall Fashion Gala alongside her husband, fellow Hollywood star Matthew Broderick. For the occasion, Parker wore a midnight blue off-the-shoulder number by Monse. The dress was made entirely out of fringe, creating plenty of fun movement as the actor walked and posed. Chic mesh heels and a dramatic smoky eye finished the fun look off, showing that sophisticated fashion can be innovative too.

When 51-year-old Sarah Jessica Parker walked the red carpet of the 2017 People’s Choice Awards, her asymmetrical gold dress was an instant attention-grabber. The J. Mendel design featured a corset bodice and off-the-shoulder sleeves alongside a layered skirt. Parker kept the rest of her look simple, rocking straight hair and her signature smoky eye. Like that, the metallic dress, which looked liquid as the star moved, had its well-deserved moment.

As a Met Gala regular, Sarah Jessica Parker is never afraid to go all out. The 53-year-old attended the 2018 Met Gala in a very dramatic and detail-oriented design by Dolce & Gabbana that featured a busy gold dress and an equally intricate large headpiece. The evening’s theme was “Heavenly Bodies: Fashion and the Catholic Imagination,” and Parker’s look certainly delivered. Among the many stars who don’t take the Met Gala themes too seriously, the “And Just Like That…” actor always ensures her look is fun and theatrical.

While muted and neutral colors are a safe go-to for many, Sarah Jessica Parker is not one to shy away from a daring color — not even in her 50s. In September 2019, the “Failure to Launch” actor showed up to the New York City Ballet Fall Fashion Gala in a fluorescent pink dress that was definitely a statement due to its bright color and its puffy silhouette. The Zac Posen design may not have been a classic choice, but the then-54-year-old clearly loved the fun piece.

At the age of 54, Sarah Jessica Parker wore yet another pouffy silhouette, this time to the 2019 GLAAD Media Awards. While this Elie Saab design wasn’t as voluminous as the pink dress she wore to the New York City Ballet Fall Fashion Gala, it still featured a daring and fun silhouette with enhanced shoulders. Apart from that, the teal and blue patterned fabric added another fun element to the look.

Metallic dresses aren’t a look we see too often, but in her 50s, Sarah Jessica Parker has shown just how fabulous they can look. In May 2019, 54-year-old Parker showed up to the press night for the West End play “The Starry Messenger,” in which her husband starred. Parker showed her support while wearing a glamorous J. Mendel design that, thanks to its pleated structure, shimmered beautifully in the light.

For the world premiere of “Hocus Pocus 2,” the sequel to the cult ’90s Halloween hit, Sarah Jessica Parker leaned into shades of purple and pink. The star showed up to the red carpet in New York City in September 2022 in a design by Armani Privé — a fun look showcasing that fashion in one’s 50s can go beyond dresses. Parker wore a gray jacket with pink and purple floral embellishments and a sparkly trim, silky lavender pants, and hot pink pointy heels.

In September 2023, Sarah Jessica Parker was photographed heading to the Daily Front Row Fashion Media Awards in New York City in a long-sleeved midi lace dress. Sounds chic? Well, it was, except it was also incredibly fun, because the Oscar de la Renta dress was in bright purple, and the Hollywood star paired it with pointy, neon green heels. Many women in their 50s might choose not to wear such a colorful look, but Parker knows that fashion is all about experimenting outside the box and, of course, having fun!