Kelly Osbourne's Worst Outfits Over The Years

From her early days in showbiz as reality TV's resident pop-punk rebel to her years spent as a red carpet commentator on E!'s "Fashion Police," Kelly Osbourne, who has undergone a complete weight-loss transformation, has never been one to shy away from experimenting with a wide range of styles. Whether it was her days leaning into edgy punk layers or embracing ultra polished couture silhouettes, the TV personality has consistently used fashion as a powerful form of self-expression. 

She has always taken her style evolution seriously, so much so that she's rarely ever seen with her natural hair color that makes her unrecognizable. The singer has reinvented her look many times, which has reinforced over and over again her reputation as a risk-taker when it comes to fashion. 

Over the years, her outfits have often been dramatic, statement-heavy, and bold. However, while the fearless approach has produced some iconic looks, it has also resulted in a handful of looks that had people scratching their heads. Whether they were out of sync with the occasion, or just plain bad, these were some of Osbourne's biggest fashion fails. 

By 2002, Kelly Osbourne was no longer just Ozzy's daughter, but a breakout star. Her family's reality show, "The Osbournes," was a massive hit, and she also released her pop-punk debut album, "Shut Up." It was clear she was fully embracing her edgy punk era when she showed up to the Teen Choice Awards in pumps, but was later spotted walking the event barefoot. While ditching the shoes might have been a comfort call, walking around a major awards show without shoes made the look feel underwhelming and inappropriate for the occasion.

In 2004, Kelly Osbourne was still heavily in her pop-punk era, and she dressed accordingly. Osbourne showed up to the "Eurotrip" world premiere in support of her friend and actor, the late Michelle Trachtenberg, but her outfit suggested a far more casual occasion. She wore a black hoodie layered over a graphic t-shirt and paired the look with a black skirt over leggings. It looked like Osbourne was ready for a casual night at the movies with friends, not a film premiere.

You'd think Kelly Osbourne would totally own the scene at the 2013 Met Gala when the theme was "Punk: Chaos to Couture." Instead, Osbourne opted for a polished black gown accented with some fringe detailing and a wide yellow belt from Marc Jacobs. Aside from being a bit disappointing, the draping of the dress was not very flattering, and the fringe was more boho than punk.

As a co-host on "Fashion Police," Kelly Osbourne had established herself as a red carpet commentator, judging celebrity outfits. That's why her appearance at the Screen Actors Guild Awards in 2014 felt surprising. Fashion aficionados know a hairstyle can make or break a look, and her lavender hair, which was one of many hair transformations for Osbourne, clashed with her deep navy gown. For someone who was okay critiquing others' style missteps, this color pairing was a serious oversight. 

Kelly Osbourne channeled "American Horror Story" vibes for Halloween in 2018 dressed up as the iconic Myrtle Snow. The dramatic red wig, red cat eye shades, sheer lace gloves, and black satin robe ensemble clearly nodded to Myrtle's signature look. However, the character was known for her couture-level flair, and this interpretation felt too simplified. A fan of the show took to the AHS subreddit to share their thoughts on the costume, writing, "Myrtle would have her crucified on a stake for shaming her with this cheap Party City interpretation." 

In May 2019, Kelly Osbourne was photographed arriving at a night club in London in the boldest and bluest power suit that certainly made an impact. The vibrant color and structured silhouette checked all the boxes of a stunning after-hours glam look. However, the sharp plunging neckline and snug tailoring pushed the ensemble into overly dramatic territory. The deep cut and overly cinched styling were vying for attention and overpowered the look. The polished blue power suit didn't stand a chance to shine.

At the 2019 American Music Awards, Kelly Osbourne donned a deep green velvet gown with a round neckline. While the rich fabric and classic silhouette were elegant, the look felt more gala than music celebration. The AMAs are usually filled with vibrantly dressed stars, but Osbourne's long-sleeved dress created a mood that leaned more serious than celebratory. And despite her purple hair and short bangs, the overall look came off as oddly matronly.