Sarah Jessica Parker Outfits That Could Have Placed Her on the Worst-Dressed List

In 1988, Sarah Jessica Parker attended the Amnesty Concert in Los Angeles looking every bit like the product of her generation. Between the overalls, the oversized blazer, the layered strands of necklaces, and what was known as “the Blossom hat” after the character Blossom (played by Mayim Bialik) in a series called “Blossom,” that ran from 1990 to 1994, Parker looked like the epitome of late 1980s to early 1990s fashion. Though this would have been a nice tribute to the beloved show, this outfit seems to be overdoing it, giving off the appearance of simply trying too hard. The future fashion icon could have easily removed a few items and still nailed peak 1980s flawlessly. 

Yes, the early 1990s were an absolute tragedy when it came to fashion, but whatever made Sarah Jessica Parker think that a pom-pom hemline would be a good idea for any occasion is perplexing. Here, Parker is seen attending the 17th Annual People’s Choice Awards in March 1991, and not only does she look uncomfortable, she looks like she got dressed in the dark. While maybe the pom-pom hemline — which appears to have a pearl finish — could be deemed a nice touch in that it matches the pearl bracelet, that’s just throwing Parker a bone. In reality, everything about this outfit and its semi bridal appearance seems underwhelming for a red carpet. But at least Parker is pulling off the pearls without looking stuffy, so that’s something.

Although by the ’90s, Sarah Jessica Parker had already been in the movie business for a few years, having roles in such 1980s’ classics like “Footloose” and “Girls Just Want to Have Fun,” it was 1992’s “Honeymoon in Vegas” that took her career to new heights. Playing opposite Nicolas Cage and the legendary James Caan, Parker proved she was a star. But when it came to attending the premiere of the film in August 1992, it was obvious she needed to hone her fashion skills. The star showed up in a simple black tank dress that she accessorized with an oversized cross pendant necklace. While there’s nothing wrong with looking like you’ve been plucked out of Madonna’s “Like A Prayer” video on Halloween, when it’s your movie premiere, you should be taking things in a whole other (read: better) direction.

Picture this: It’s 1999 and you’ve just received an invitation to Rosie O’Donnell’s “For All Kids Foundation’s 2nd Annual White Rose Awards Gala.” Because you’re all about charitable events, you decide to go and dig out the most appropriate thing from your closet to wear. What do you choose? If you’re Sarah Jessica Parker, you go for a monochromatic white look that shows just enough midriff and has sleeves that extend a good six inches past where your fingers end. If this extra-long sleeve thing was a trend of 1999, there might be some sense to be made, but because it wasn’t, it just looks sloppy and like the most universally flattering clothing hack has been disregarded: tailoring.

By 2000, “Sex and the City” had already been on the air for two years. Despite that, it’s star, Sarah Jessica Parker, showed up to Talk Magazine Party with her SATC costar, Chris Noth, wearing whatever this is. If we take it apart, it looks like a silky skirt paired with a ruffly, pirate-inspired white shirt. To complete this eye sore, Parker has added an off-white cardigan to the mix and shoved a rose down the front of the shirt. Even Parker looks extremely confused about what’s going on here.

If ever there was a time in fashion history that evokes the word “no,” and nothing more, this is it. Everything about this pink and white dress — and the pale aqua bauble necklace — evokes White Wine Wednesdays with the neighborhood ladies and not even in a good way. What makes this look even worse is that the dress is by Oscar De La Renta, who was still very much alive in June 2004, and for the Fragrance Foundation’s 32nd Annual ‘FIFI’ Awards at Hammerstein Ballroom — in New York City, no less. Sarah Jessica Parker may have been born in a Midwest town of less than 5,000 people, but you don’t dress that way for anything that’s being held at the iconic Hammerstein Ballroom.

If you’re looking at this photo wondering what the Met Gala theme is supposed to be, you’re probably not alone. Although the backdrop is definitely for something HBO-related, what Sarah Jessica Parker is wearing and her hairstyle suggests there’s a theme and she has woefully missed the mark. However, there’s no theme, nor is there a gala. Instead, it’s the HBO Golden Globes After-Party at Circa 55 at Beverly Hilton Hotel in January 2017 and Parker, who was starring in HBO’s “Divorce” at the time, thought this white almost wedding-like gown was the best look for the occasion. Perhaps it was an attempt at method dressing as a means to promote the series “Divorce,” because you need a wedding before you can have a divorce, but even if that’s the case, it still doesn’t make sense.

In September 2019, for the 8th Annual New York City Ballet Fall Fashion Gala at David H. Koch Theater, Sarah Jessica Parker went full Carrie Bradshaw when she wore this Zac Posen design. It’s just a lot for the ballet, especially when the attention should be on the dancers and not the woman in hot pink taffeta strolling up the red carpet in mismatched shoes. In 2022, Parker participated in Vogue’s video series, “Life in Looks,” in which she talked about her love for this dress and the shoes. While it’s great Parker loved the look so much, this loud number still deserves a spot on the worst-dressed list.

Because she felt she hadn’t exhausted the mismatching shoe look enough in 2019, Sarah Jessica Parker attended the New York City Ballet Fall Fashion Gala in October 2023, trying to pull off the same thing, but in a Carolina Herrera dress that was notably less bright. While Parker certainly gets points for embracing the coquette beauty trend that was big in 2023 thanks to her hair bows, the rest of the ensemble comes off as childish and out of place. Parker looks like she’s off to the clubs in the Meatpacking District for a friend’s bachelorette party, instead of the ballet’s fashion gala.

To promote the third season of “And Just Like That…” on HBO, Sarah Jessica Parker appeared on the Good Morning America in May 2025, looking like she had a lost a fight with the artist Yayoi Kusama. While Kusama will never concede that something can contain too many dots, this blue and white suit — with an ankle-length skirt — proves otherwise. It’s also too business-looking for any early morning show and too serious for promoting a comedy series or film of any kind. Also, the open-toe white heels weren’t helping the situation at all, as they are one of many outdated shoe trends we’ve left back in the 2010s. At the rate things are going, it might be the last season of “And Just Like That…” SJP, so you might as well bring some Carrie style fashion sense to the interviews.