Molly Ringwald Has Donned A Few Red Carpet Fashion Flops Over The Years

When you are in the public eye for decades, like Molly Ringwald, it's inevitable you'll be exposed to some scrutiny. After all, there are only so many red carpets you can attend without landing on a worst-dressed list somewhere. The "Sixteen Candles" star has always had a bold approach to style — and created some iconic fashion moments in "Pretty in Pink" — but even she has had some flops over the years.

Ringwald has had a stunning transformation since her time as a teen star in the '80s and is still gorgeous in her later, adult roles like in "Riverdale" and "Montauk." Her style is vintage and thrifty. "As much as I can, I try to buy stuff that's old, that's been worn before, or consignment stuff on principle," she told Coveteur in April 2024. Ringwald added, "I ... really love vintage. I still scour every thrift store I can when I have the chance."

That said, Ringwald has sometimes worn pieces that just don't work well together and chosen colors of clothes that don't make her look her best. It's clear that some of these fashion flops would have been better left on the rack.

Molly Ringwald attended the "Tomorrow Is Tonight: Project A.L.S." benefit in October 2000, looking like she was ready for prom night. She wore a dress with a black halter top and a long, hot pink skirt with matching band around her waist. A black shawl was draped around her elbows, and she accessorized with a black clutch and a triple strand of oversized, gold pearl necklaces. We know pink is her color, but she would have been better off with a more grown-up looking outfit here.

Molly Ringwald looked ready to jet-set off to Hawaii in this outfit, which she wore to the 12^th Annual GLAAD Media Awards in April 2001. In a photo from the event, Ringwald sported a blond wig with Shirley Temple-like ringlets, with a big white flower tucked into her ear. This flower matched the oversized white flowers on her red dress, giving a total Hawaiian vibe that just didn't make sense for the occasion. (Or any occasion, except for maybe a luau.)

Sometimes, Molly Ringwald's fashion has been just plain boring. Enter: the dress she wore to the Princess Grace Awards Gala in October 2004. Her light beige dress blended perfectly with her skin tone, making her look washed out and pale. The dress itself was nothing to write home about, as it was just a simple, short-sleeved frock with some embellishments, a tie under her bust, and tassels hanging off the end. The finished outfit was paired with beige tights and champagne-colored shoes.

When Molly Ringwald attended The Vulture Spot at the Sundance Film Festival in January 2026, she seemingly got dressed in the dark. Her maroon dress clashed with the bright-red sweater tied around her waist. The dress was awkward, with a long white button-down shirt underneath the dress, and black tights and boots. Ringwald herself looked beautiful as ever, of course, especially as the darker fall color looked great with her skin tone.

Deadpool may be an anti-hero, but Molly Ringwald's outfit was the true villain at a "Deadpool" fan event in February 2016. On the red carpet, she had a white blouse underneath a black top with a big white bow tied around the collar. This was tucked into a long, navy-blue skirt, with a red windowpane pattern that matched the bright red of her hat. We're not exactly sure what she was going for with this look, but we know it wasn't pulled off.

While dresses over jeans were popular in the 2000s, Molly Ringwald's version seemed off. At the MTV Movie Awards in June 2005, she wore a light pink mini dress with gold details (including a sparkly gold belt) that was extremely low-cut to show off her ample cleavage. Instead of wearing it over jeans, she paired it with white capri pants and white heels. She looked like she was trying to dress like a teenager.

We appreciate the effort Molly Ringwald put in to look bold at the Planned Parenthood of Greater New York Gala in April 2024. However, it would have looked better if she picked either an eye-catching top or a shocking skirt — not both! On the red carpet, Ringwald wore a bright orange, palm tree-print blouse tucked into a shiny silver metallic pencil skirt. Her beige shoes were the only things not fighting for attention with this look.

Molly Ringwald's fashion accessories stood out in a bad way at the premiere of "Spirited" in November 2022. At the event, she wore a black dress with asymmetrical embroidery in different colored threads. The dress itself was fine (if a little strange), but the jarring bright-red tights and silver shoes she paired it with definitely seemed like an odd choice. Her clutch also didn't really go with the rest of the outfit with its yellow and red flowers on black fabric.

Clearly, Molly Ringwald is a fan of tassels, as she wore them again at the Broadway premiere of "Modern Orthodox" in December 2004. Her dress was one of the vintage '70s styles that look bizarre in the modern era with its eyesore of patterns in yellow, brown, dark orange, gray, and white, complete with gold tassels along the hemline. Did she repurpose old curtains to create this dress? Even the shape was boring, with its three-quarters sleeves and straight body that didn't accentuate her body at all.