Kelly Osbourne Makeup Fails That Will Haunt Her Forever

As the daughter of the late Black Sabbath frontman, Ozzy Osbourne, and TV host, Sharon Osbourne, Kelly Osbourne has had eyes on her since she can remember. After hosting "Fashion Police" and guest-judging on "Project Runway," you would assume that a leading figure in fashion would know their way around a makeup brush. However, staying on the cutting edge of the hottest trends can sometimes be a double-edged sword, leading you to experiment and broaden your aesthetic horizon into some ... questionable directions.

Kelly's makeup artist in 2015, John Stapleton, addressed the star's risky makeup choices in an interview with Lifestyle.INQ, acknowledging how "I would definitely try to steer someone out of fire. It's important for my reputation to hold true. ... With some clients, I am close enough to [be honest]. Like with Kelly [Osbourne], there are times that it's a hit while there are times that it's a miss." It's important to note that, with a figure as daring and arguably avant-garde as Kelly, there have definitely been some extreme looks that, being inherently bold, aren't technically badly executed. No stranger to some mod-inspired eye looks, a punk panda eye, and metallic eyeshadow reaching to her temples, one cannot mistake an artistic look for an all-out fail. However, even in experimenting, there were definitely some haunting cosmetic catastrophes that Kelly has had to brush off.

If Kelly Osbourne was trying to channel a messy look, then consider her mission accomplished. At the 2003 "Red Party" To Benefit The Life Through Art Foundation, Osbourne was channeling Ke$ha six years before the release of her trash-anthem "Tik Tok". The glittery smoky panda eye, clumpy mascara, single cigarette earring, and overlined hot pink lip all came together to create a messy look, but arguably unintentionally. Her smudged eyeshadow seemingly bled into her under-eye area, and the lip liner was uneven and smudged. The bolder you go, the harder you fall. 

While appearing at the party for her first-ever CosmoGirl cover in July 2002, Kelly Osbourne's vintage-inspired look seemingly couldn't take the weight of the event. While the dramatic cut-crease would suggest another of her infamous Twiggy-inspired eye looks, you could hardly see it through a thick wall of false lashes. Some slight trimming would have given her the same wispy effect, but with a lot more visibility for the rest of her look. Heavy lashes made the pop singer look tired at the dawn of Osbourne's messy history of controversy. 

While an overextended wing was definitely a stylistic choice, the main issue with Kelly Osbourne's dramatic eyeliner at the 2011 Grammy Awards BMG after party was its inconsistency. Shorter wings hardly need geometric precision to look even, but when your eyeliner is reaching all the way back to the tops of your ears, there better not be any bumps in the road. That being said, a quick swipe of a Q-tip or concealer would have helped to make the liner more even and concise. It seems like in the years since, Osbourne has learned that restraint can go a long way. 

Although Kelly Osbourne hadn't had the most polished makeup looks up until this point, this 2012 look at The Art of Elysium's HEAVEN event proved that color theory can be just as damning. While her eye look, blush, brows, and lipstick application are technically on point, the glaringly obvious makeup mismatch is almost nauseating. With a yellow base that stood out against her neck, Osbourne's pastel pink lip only accentuated her clashing complexion. Despite looking tonally off, Osbourne appeared more like herself than when she would eventually be dodging plastic surgery rumors.

A red lip is easily one of the most common culprits for makeup mistakes — whether it's on your teeth, running down your face, or managing to find its way onto the closest white article of clothing. Kelly Osbourne's solution at her 2003 "Top of the Pops" premiere in London? Just do the dirty work for it. While Osbourne had shown some lipliner proficiency in her previous looks, it appears as though the product hadn't been invited to the event at all. Opting to apply the bold color on her lip (and seemingly beyond), the result was more Miranda Sings than pop star. 

Posing alongside her brother and one of Rod Stewart's eight kids back in 2001, Kelly Osbourne looks drastically done-up and dressed down all at once. With her face seemingly foundation-free and without a signature bold lip, Osbourne's eye makeup can't help but stand out in this top-heavy look. Her eyeshadow had been applied without any solid base, leaving some stray brow hairs to peek through over her bold liner. While it might have been an issue of skill, the rounded winged liner looks too blunt to be aerodynamic. 

While Kelly Osbourne's transformation has been hard to believe over the last two decades in the public eye, one thing that never quite changed was her big, expressive smile. Osbourne was clearly elated at the release of her 2002 album, "Shut Up," but her makeup was far from cause for celebration. Her hot pink lipstick kept it relatively together, but couldn't quite cooperate with her teal and lime-green Chanel blazer. She was seemingly still finding her grip on her eyeliner, with the white wing making the shaky application of the thin black lines pop to the forefront.