Kelly Osbourne's Fashion Evolution Is Quite the Wild Ride

Kelly Osbourne has never been one to mince f--king words. 

And now that becoming a mom to 23-month-old Sidney with Slipknot musician boyfriend Sid Wilson has transformed her "in every way that you can possibly be changed," as Kelly put it on Today last May, she can't be bothered to worry about what others think—particularly when it comes to her fashions.

Not that she let it stress her out all that much before. 

"Not everyone's going to like everything everyone wears," she reasoned during a 2012 appearance on Today. "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?"

On any given day for Kelly (now rocking platinum strands after a long stretch with her preferred violet hue), that might mean black jeans, black heels and a black biker jacket or something like the ivory midi from Nicky Hilton's collab with Rebecca Vallance that had The Osbournes Podcast host declaring she was "feeling rather feminine."

And the middle of Black Sabbath rocker Ozzy Osbourne and America's Got Talent alum Sharon Osbourne's three kids has a long history of leaning into what feels right. 

"My mom says, ever since I was a kid, I knew what I wanted to wear and I just wore it," she recounted to Coveteur in 2014. "I remeber being a kid in Santa Monica at Fred Segal and there was this green suit that made me look like a walking boogie. It had a waistcoat. It was serious. I asked my mom, 'Please, please, please can I have it?' And she said, 'No, it's gross, smelly and you're not having it.' Plus, it's expensive, but we bought it and I still have it to this day." 

So no surprise her advice to the outlet was to dress however the f--k you want. 

"Wear it because it makes you feel wonderful," she advised. "Wear it because it makes you feel confident. Don't wear it because you think you're going to attract someone else. If you don't like something, you don't have to wear it. If you wear something someone else doesn't like, who gives a s--t! They don't have to wear it." 

And Kelly, meanwhile, will be rocking everything from sequined pants to a ruffled frock. 

"I look back on some photos now and say, 'OMG,'" she admitted of her two decades in the public eye. "That's the fun in fashion. Through your clothes you can make yourself be whoever you want to be." 

Celebrate her turning the big 4-0 Oct. 27 by checking out every last persona she's brought to the red carpet. 

Kelly Osbourne took grunge beauty to new heights in a blunt haircut and smoldering eye makeup to sign copies of her debut disc Shut Up at Tower Records in Los Angeles.

At the MTV Movie Awards, the 2000s princess of rock and roll wore a strapless black dress that draped across her hips.

Kelly's dichromatic bob and fur-lined bust were Cruella-coded at the American Music Awards.

Kelly was spooky season ready wearing a black gown with lace detailing at her 21st birthday party. 

Adding a pop to her usual black and white uniform, Kelly accessorized with gold accents at the Denis Simachev fashion show in London.

At the Us Weekly Hot Hollywood Awards, the "Changes" singer opted for a prim, cream-colored crochet dress.

Kelly's red carpet style began to bloom at the Bafta Television Awards, where she was donned a poofy white dress marked with a floral pattern.

A closer cropped Kelly made an appearance at the Shockwaves NME Awards in sequins and standout makeup.

Kelly's full skirt and extreme shoulder pads made a red carpet statement at the Sony Radio Academy Awards in London.

Wearing a floor-length embroidered dress, Kelly went elegant for the Glamour Women Of The Year Awards.

Petal appliqués on each arm gave new meaning to the term flower power as Kelly walked the carpet at Teen Vogue's Young Hollywood party.

The Fashion Police panelist looked ready to take no prisoners in this little latex number at the L.A.M.B. Fall presentation.

At the Emmys, Kelly opted for a body-hugging Tony Ward frock. 

Kelly played with texture and prints to come up with this eye-catching combo for the Spike TV Scream Awards.

Ozzy Osbourne and Sharon Osbourne's middle child went with a sexy black lace dress, peep-toe heels and big hair for her appearance at the American Music Awards.

The fashion correspondent attended the Golden Globes in a dramatic Zac Posen gown, Casadei heels and Kimberly McDonald jewelry. 

Kelly secured her front-row fashionista status at Anna Sui's Spring 2011 show rocking a modern-day pompadour with a sequined vest.

Kelly was a breath of fresh air in a ruffled-to-the-max Tadashi mini, bedazzled Alexander McQueen heels and Forevermark ear bling at the Grammy Awards.

For the Badgley Mischka Fall 2011 show, she opted for a sheer dress offset by a black belt, fitted leather blazer and pumps.

The Fashion Police alum selected Tony Ward for her appearance at Elton John's Oscars viewing party. 

For a Southern Style event, Kelly slipped into an LBD.  

The face of Madonna's Material Girl got bright and cheery during Fashion's Night Out.

Going glam for TV's big night, Kelly worked the Emmys carpet in a burgundy J. Mendel gown and Katerina Maxine jewels. 

Kelly attended the 5th Annual Art of Elysium Heaven Gala in LA in a grey and black gown.

At the Golden Globes, she was sleek and chic in a blue Zac Posen gown.

Continuing her run of elegant red carpet gowns, she picked this Badgley Mischka gown with an embellished shoulder detail and tassel belt, paired with Amrapali and Palladium jewels for the SAG Awards.

She rocked a black single-shoulder Tony Ward frock with fabulous fuchsia Giuseppi Zanotti platform heels and her pale purple 'do to the 2012 Kids' Choice Awards.

Kelly skipped her shirt and showed some skin for the Topshop launch party in Hollywood.

The former TV host wowed on the Oscars red carpet in a flowing, black Tony Ward Couture gown with ombré sparkles.

The E! alum took us back to high school in a monogrammed letterman jacket and leather miniskirt for a Lucky event.

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