The Riskiest Red-Carpet Looks Of The 2020s

Stars have to bring it when dressing for premieres and awards shows, as they don't want to end up on any worst-dressed celeb red carpet list. Some play it safe, like Jennifer Aniston, who is known for her love of LBDs. Not one to favor daring looks, the "Friends" star has stuck with her signature girl-next-door aesthetic, and it works for her. However, there are others who go big or go home, taking fashion risks like no others. When thinking of jaw-dropping 'fits, Jennifer Lopez's low-cut green Versace gown she wore to the 2000 Grammy Awards comes to mind, which remains one of her best looks to date. 20 years later, many celebrities have attempted — and succeeded — to steal the show as well.

The 2020s were full of bold pieces on the red carpet, and the outfits themselves have become the stuff of legend. While some weren't necessarily the best in terms of design, we applaud the stars who took the sartorial leap. Whether it's an unusually structured frock or a sexy peekaboo style, these famous faces rocked iconic looks that had people talking.

Saoirse Ronan loves taking fashion risks on the red carpet, and she didn't disappoint at the 2020 Oscars. Her black and cream Gucci gown featured a large peplum waist and a plunging V-neck with a bright periwinkle skirt. While many might not think to pair such contrasting colors, the combo worked on the "Little Women" star. A fun fact about her gown — the top half was recycled from her BAFTAs frock, proving that Ronan's not afraid to wear something twice on the red carpet.

Jennifer Lopez has had some of the sexiest red carpet looks ever, but she went more avant-garde at the 2020 Golden Globes. The pop star showed up dressed like a wrapped present in a Valentino gown that had a large green and gold bow on the bodice. The look was anything but subtle, and we don't expect anything less from Lopez, who was nominated that year for her role in "Hustlers." When speaking about her choice of dress to Extra, Lopez stated, "Green is my lucky color." Unfortunately, she didn't win that night, but at least she took a fashion risk and really went for it.

Celebrities who wear Schiaparelli do so to make a statement, which is what Bella Hadid did at the 2021 Cannes Film Festival. The model donned a daring black gown with a low-cut chest and a giant gold necklace, modeled after human lungs, that covered her breasts. While Hadid confidently strutted the red carpet for the "Tre Piani" premiere, she admitted later that she was nervous. "I was really worried about how it would hold," Hadid told Vogue. She added, "It was very bizarre walking onto the carpet in places you wouldn't usually have a breeze."

Is Cardi B the drama? She certainly was while walking the red carpet at the 2021 American Music Awards. The rapper showed up in a structured black Schiaparelli gown that was gorgeously gothic. However, her biggest statement pieces were a shiny gold mask and a voluminous sheer veil draped over her face. Adding to the dramatic look was a pair of long black gloves featuring spiky gold fingernail tips. As the show's host that year, her red carpet look was just one of Cardi B's many outfits, but was definitely the most memorable.

Florence Pugh made sure to turn heads at the "Don't Worry Darling" premiere at the Venice Film Festival in 2022 with her dazzling sheer Valentino Haute Couture gown. The "Thunderbolts" star was all legs in a pair of black short shorts, layered underneath an embellished overlay, accented with big puffy sleeves and an open front. Adding to Pugh's glamorous outfit were pointy black pumps decorated with feathers, sealed with a bow wrapped around her ankle. If the actor was aiming to make an entrance, she definitely did so.

Fans of Hunter Schafer know that she's all about fashion and can rely on her to stay undeniably fierce, even in her more outlandish choices. In 2023, the "Euphoria" star had jaws on the floor when she arrived at the Vanity Fair Oscar party wearing a large white feather strapped around her chest. Schafer paired the tiny top with a low-waist satin maxi skirt slung low on her hips, showing off her toned abs. The model's stylist, Law Roach, shared the look on Instagram, and fans were all for the peekaboo ensemble. Proving that Schafer is a total style icon, one declared, "A GRAND mf closing if there ever was one!!!"

Some celebs completely ignored the 2024 Met Gala theme, "Garden of Time," but not Tyla. The singer showed up as a literal hourglass in a form-fitting Balmain gown entirely made of sand. The dress was molded to her body and had an organic feel, with an uneven cut at the top and a flowing train. To go with the theme, Tyla carried an hourglass filled with sand and had sprinkles of gold glitter on her shoulder and arm. The "Water" singer told Vogue that it took Balmain about two months to make the creation just for her, revealing, "They molded it to fit me perfectly."

Zendaya always slays the red carpet, but she truly stunned during the "Dune 2" premiere in London. The fashionista looked like a futuristic, otherworldly being in a metal Thierry Mugler suit with several racy cutouts throughout the body, including a couple of round ones on her behind. It was an epic moment that seldom happens, as Zendaya told Vogue that she felt like passing out after trying it on. "The metal conducts and holds onto heat very quickly and kind of traps heat in," she shared. Ultimately, Zendaya chanced it for "Dune 2," and thankfully, she made the red carpet walk without fainting.

Stars are usually dripping in jewels at awards shows, but Jenna Ortega literally draped herself in baubles at the 2025 Emmy Awards. The "Wednesday" star wore a Givenchy top made entirely of large gemstones and nothing else, resulting in a bold peekaboo look. Ortega paired the top with a plain black skirt with a thigh-high slit and strappy black platform sandals, which allowed the top to shine as the main star of the show. The look will go down in history as one of the best awards show outfits of all time.