6 Celebs Who Got The Last Laugh When Their 'Worst-Dressed' Moments Became Iconic

Celebrities usually wow the public with their fashion choices, but sometimes, their style doesn't live up to the occasion. In response to these mishaps, the press curates "worst-dressed" celebrity lists to help people avoid making similar mistakes. For instance, some of the worst-dressed celebs at the 2026 Met Gala should have worn those outfits at more casual events. On the flip side, experimenting with their fashion sense might also cost an A-lister on the red carpet. However, some stars actually wear outfits that don't deserve to be on worst-dressed round-ups, even if it takes a while for the public to see the light.

Sometimes, celebrities walk on the red carpet in outfits that seemingly nobody else would wear. Whether they're showing more skin than others or incorporating certain colors and textures into their look, breaking from the norm can be polarizing. Famous people who choose daring red carpet looks might receive more criticism right after the event compared to the distant future. From the '90s to the mid-2010s, these six celebrities had outfits that landed on a "worst-dressed" list but were vindicated with public approval years later.

Jennifer Lopez is known for turning heads on the red carpet, whether or not the people approve of her style. Although some of J.Lo's outfits missed the mark, others were disliked simply because of how revealing they were. At the 2009 Golden Globe awards, Lopez wore a gold, backless Marchesa gown with fabric that plunged at her chest. In 2014, Fox News criticized it while assessing the fashion of the 2009 Golden Globes, calling it "a bit much." However, the criticism didn't last longer than a decade. Time Magazine included the shimmery dress in a list of Lopez's best red carpet outfits in 2020.

Katy Perry has worn some inappropriate outfits, but she faced criticism over the tame dress she wore to the 2009 VMAs. It was a silver minidress with spikes on the sides of her waist and hips. SheKnows considered it one of the worst looks in VMAs history and said, "If there was just a little more to Katy Perry's VMA dress in 2009, she could have pulled this look off." In reality, the "California Gurls" singer stunned in a look that satisfied her bold energy and matched her fellow celebrities' edgy attire.

In February 2009, Paris Hilton went to the 51^st annual Grammy Awards. The heiress wore a color block minidress, with purple fabric on the bust and dark purple sheer fabric over the green skirt. The hem of the sheer detail was light green lace. Marie Claire scrutinized her for wearing a short dress by comparing it to a pajama shirt. The outlet wrote, "We hate to sound like your mum, Paris, but where's the bottom half of your outfit?"

Hilton's fashion risk paid off years later. In 2022, an Instagram account dedicated to celebrity nostalgia posted a carousel of the heiress' purple and green dress. Some users asked for details about the gown while others compared it to the iconic "13 Going on 30" dress. One comment read, "She dropped this," followed by a crown emoji.

Rihanna usually leaves everyone speechless on the red carpet, but she got backlash for her look at the 2014 Met Gala. The artist-turned-entrepreneur wore a white two-piece set by Stella McCartney with a sheer, silver-encrusted collar. She also wore her black curls in a high, loose bun. The New York Post wasn't fond of her set or her hair, but other publications showed Rihanna some love. A 2015 Forbes article put her outfit on their list of "Unforgettable Met Gala Dresses." Although this dress isn't as memorable as Rihanna's other Met Gala looks, the singer picked a style that flattered her very well.

Canadian singer Celine Dion attended the Oscars with her husband and manager René Angélil in 1999. Dion showed off her back by wearing her white tux backwards. She also wore matching white pants, a white hat, and sunglasses with silver gems. In 2011, Glamour put Dion's look on its list of worst red carpet outfits. The magazine said, "[E]verything about this screams overkill," referring to the brightness of the outfit and the shape of the hat. Despite the backlash, backward clothing became a trend in 2026, which certifies the 1999 Oscars as one of Dion's best fashion moments.

Cher has a thing for daring outfits, and sometimes people appreciate her style well after she wore a look. In 1998, the singer went to the Oscars in a white sheer gown with off-the-shoulder sleeves. Cher accessorized with a matching headpiece, a crystal choker, silver heels, and a silver coin purse. Fashion designer Mr. Blackwell put her at the top of his worst-dressed list that year and described her outfit as, "A million beads and one over-exposed derriere" (via Salon). E! News later put Cher on their list of the worst-ever Oscars outfits, but sheer dresses became popular in the 2020s. 

In 2025, Vogue Brazil celebrated its 50^th anniversary at the Vogue Ball, and guests recreated iconic red carpet looks. Brazilian influencer Mileide Mihaile wore a sheer dress and headpiece very similar to Cher's look, and raved about Cher's star power on Instagram. The recreation taking place almost thirty years later definitely vindicated the singer's affinity for avant-garde fashion.