Kelly Osbourne's Best-Dressed Moments Are An Eclectic Mix Of Outfits

As the daughter of rock legend Ozzy Osbourne and television star Sharon Osbourne, Kelly Osbourne has always been destined for fame. In the early aughts, teen Kelly drew attention to herself thanks to her punk-rock aesthetic and her aspiring music career. However, the star has come a long way since covering Madonna's "Papa Don't Preach"; in fact, Kelly Osbourne's stunning style evolution from punk princess to refined fashionista showcases her numerous fashion eras.

Throughout her career, Osbourne has taken many fashion risks, always exploring trends she likes. In 2012, she explained to Today that for her, it's all about how she feels about a clothing item. "Not everyone's going to like everything everyone wears," the reality star explained. "You've just got to wear what you like and that's all that matters. At the end of the day, who cares what I think of what you're wearing?" Now, while not every 'fit the star has worn has been immaculate, some of her best looks showcase the variety of styles that Kelly Osbourne can pull off.

Kelly Osbourne showed up to the 2013 Golden Globe Awards in a strapless mermaid dress, a Zac Posen design. The look was classic and chic, while the barely-there green color of the fabric was a modern and unexpected choice. Paired with Osbourne's at-the-time pastel lavender hair, the glamorous fashion moment offered plenty of color. Kelly Osbourne has gone through a stunning hair transformation, and purple is understandably one of her favorite hues.

When Kelly Osbourne showed up to the 2024 Grammys red carpet, her look was the epitome of glamorous gothic fashion. The star wore a strapless black gown by Christian Siriano, which featured a sheer bodice and mermaid skirt. The look was structured and chic, and paired with the star's bright purple hair, it was just the right amount of edgy. Osbourne accessorized the look with a quirky radio bag for an unexpected detail. 

Back in 2005, Kelly Osbourne attended the annual Brit Awards. For the night, the musician swapped her usual rockstar aesthetic for a slightly more sophisticated look. She wore a red A-line midi dress, which she paired with matching red heels and lipstick. Osbourne threw a white cropped cardigan over her shoulders — a Y2K staple. Paired with the singer's short black bob and blunt bangs, the look was subtly channeling retro '50s fashion.

Kelly Osbourne attended the 2018 Life Ball in Vienna, Austria, where she wore a black pleated gown with a large buckled waist belt. The garment created an unexpected silhouette, and Osbourne opted to let it shine without too many accessories. The musician wore her gray hair in a voluminous updo, ensuring the neckline of the dress had its big moment. In 2014, Osbourne told Coveteur that she always had opinions on fashion. "My mom says, ever since I was a kid, I knew what I wanted to wear and I just wore it," the star revealed (via E! News).

Kelly Osbourne attended the 2026 Grammy Awards in a simple black halter-neck gown featuring tiny polka dots that created an almost sparkly effect. The "Fashion Police" star paired the dress with a platinum-blond wig with its ends flipped out. Osbourne kept the rest of her look rather simple, adding minimal makeup and a silver clutch to the look. However, the combination of her styling and the showstopping dress was enough to create an impactful fashion and beauty moment.

Back in 2002, Kelly Osbourne attended the Creative Arts Emmy Awards, where she rocked a daring mix of colors, textures, and styles. The star, who had short black hair styled in a deep side part at the time, wore a satin yellow dress with lace and ruching. The garment was interesting enough to be worn on its own, but back in the 2000s, no outfit was complete without fun accessories. Osbourne paired the yellow dress with a fun book-cover bag and a large orange flower in her hair.

During the late 2000s, Kelly Osbourne slowly shifted from her punk-rock style to a more classic look. In 2008, she showed up to the Brit Awards in a dress that perfectly encapsulated that transition. The dress featured red, green, yellow, and black sections, and the star paired it with bold makeup. In fact, Kelly Osbourne is the queen of dramatic makeup looks, so mixing a red lip with a smoky eye is on brand for her.

By the 2020s, Kelly Osbourne was definitely known as a fashionista, and the star used any red carpet as an opportunity to remind us that her style is constantly evolving. In early 2020, she attended the premiere of the reality competition "RuPaul's Drag Race Live!" in Las Vegas, Nevada. The star wore a form-fitting, long-sleeved black gown with a white polka dot pattern. Paired with an edgy short purple bob, the look was yet another example of Osbourne's eclectic style.

In 2019, Kelly Osbourne showed up to the annual Emmy Awards in a black Brandon Maxwell gown that featured revealing cutouts. The look was simple and minimalist; however, Osbourne's purple hair added a touch of fun to the look. Back in 2012, the star told Glamour that her mother ignited her interest in fashion. "My mum has all these old books from the sixties, books on design and things — she's kept everything — and I've always looked through those," she explained.

In summer 2023, Kelly Osbourne was photographed heading out to dinner in Los Angeles, California, in an eye-catching leopard-print maxi dress. The garment featured long sleeves and a revealing neckline, and Osbourne paired it with pointy black heels and a matching bag. To make the 'fit a tad more dramatic, Osbourne added cat-eye glasses, showcasing once again that fashion is all about having fun with mixing and matching.