Jarring Photos Of Kelly Osbourne's Most Drastic Makeup Looks Over The Years

Kelly Osbourne's makeup journey has been a fascinating rollercoaster of intensity, exploration, and self expression. Looking back at her most drastic looks over the years, viewers are able to reflect on the contextual shifts in makeup culture and trends that peak through Osbourne's often striking application, giving us a glimpse into a pre-social media world where preference, environment, and discretion were one's leading guides in the world of makeup.

In the current social media landscape, a cosmetics consumer can rarely scroll through their feed without encountering a makeup review, tutorial, or "Get Ready With Me" posted by an influencer, professional makeup artist, or user who knows their way around an eyeshadow palette. Since the rise of "Beauty Gurus" on Youtube in the mid 2010s, there has been a wealth of technical instruction and product recommendations made available for the average makeup user. Easier access to knowledge came with its benefits, but it did also become a breeding ground for widespread trends, expectations of uniformity, and an increasingly small margin for error for beginners seeking to share their looks online.

Flash back to the early 2000s, when Kelly Osbourne's youth was full of risky style choices rooted in counterculture and rock aesthetics. She marched to the beat of her own drum, jarring as the outcome might have been, and wore makeup looks that pushed against norms. As she matured, she shifted to more balanced looks but largely maintained the refreshing practice of including at least one striking element. In a world of ever increasing homogeny in the makeup space, Osbourne's cosmetic preferences display uniqueness and character often lost on red carpets.

Proportions play a huge role in makeup, and it is important to take one's own features and goals into consideration when making decisions about products and how they are applied. In the case of Kelly Osbourne's makeup look at MTV's "TRL," her look appears out of proportion to viewers because of the heaviness of her false eyelashes, eyeliner, and blush.

The thick bar of black eyeliner, coupled with the oversized lashes, gives the eye a drastic yet droopy effect. But the drama doesn't stop at eye level. Osbourne's selection of a midtone, rosy blush would have been innocuous in normal amounts, but she laid it heavily on the apples of her cheeks, which quickly shifted her appearance away from lively and flushed to overly blushed.

Kelly Osbourne is not one for subtlety and never has been. She is proud of her unconventional aesthetic and acknowledges that her look is not for everyone, which is a mindset that puts her makeup choices into context. Instead of worrying about what methods of application would look "most flattering" on her features, she chooses to wear whatever strikes her fancy, regardless of whether others consider it to be too intense or overpowering.

At the CosmoGirl cover party in 2002, Osbourne opted for a dramatic black and gray cut crease that definitely demanded attention. She paired the sharp, intense eyeshadow with an equally intense lash that weighed down the corners of her eyes. Applying false eyelashes at a higher angle on the outer corner or choosing a lash shape that doesn't flare out could have helped Osbourne avoid that droop.

Kelly Osbourne's proclivity for heavy blush was an enduring trait throughout her makeup journey in the early 2000s. For the 54th Annual Primetime Emmy Awards after-party in 2002, Osbourne leaned in heavily to her preference for high intensity and went to town with pink blush all over her cheeks.

The drastic nature of the look doesn't end at the blush, though. The black, glittery, geometric eyeshadow also demands attention, and as if two startling aspects weren't enough, the matte, hot pink lips also draw the eye in, making this look a jarring compilation of dramatic features.

Though Kelly Osbourne has a soft spot in her heart for black eyeshadow, she doesn't shy away from color. At the 2002 MTV Video Music Awards, Osbourne sported a wash of canary yellow eyeshadow that extended above her brow. She left the false lashes at home, opting instead for a sensible coat of mascara and a soft line of green eyeliner that brought out the earthy tones in her eyes.

The eyes on their own were edgy, artsy, and cool, but instead of sticking to just one primary color for his look, Osbourne added a fire engine red lipstick for extra flair. The addition was bold, but not in a way that was easy on the eyes.

The early 2000s were a time of grungy experimentation for Kelly Osbourne, and she wasn't afraid of pushing the envelope on the red carpet. For the 2002 Teen Choice Awards, she sported a red, monochromatic eye and lip look that was graphic to say the least.

The circularly applied eyeshadow wrapped around her entire eye, and the only variation in color and definition came from a thinly applied line of black eyeliner across her upper lash line. For added effect, she included a red strip lash that matched the eyeshadow.

No one can say that Kelly Osbourne doesn't show range in her makeup choices. At the 2002 screening of "Die Another Day," Osbourne departed from her usual practice of applying heavy eyeshadow and opted for a bottom-heavy look, allowing the focus to remain solely on her dramatic red lips.

She left her eyes nearly bare and added only a slight flick of black eyeliner, a soft layer of mascara, and a gentle wash of shimmery champagne eyeshadow. The overall impression of this look was minimalistic, classic, and timeless, which was a striking shift from her past red carpet appearances.

Kelly Osbourne doesn't shy away from wearing a whole face full of bold makeup. During a visit to the AOL Music Green Room with her mother, Sharon Osbourne, she put together a look that featured both a solid, minimally blended application of matte gray eyeshadow, bright red lipstick, and equally striking red blush.

The eyes and lips once again competed for attention, making it difficult for viewers to decide where to look. Someone more concerned about abiding by the strictures of traditional makeup application might have opted for following the well-known tips and tricks for applying eye makeup with a bold lip or, conversely, opted for a neutral-leaning, peachy lip color, but Osbourne saw no reason to compromise on theatrics.

Kelly Osbourne didn't constrain herself to the run-of-the-mill eyeliner shapes at the Grammy after-party in 2003. Instead of a typical wing, flick, or bar over her lashline, Osbourne extended a thick, squared-off line all the way to her temples, giving her eye look an element of extremeness not often seen on the faces of celebrities.

She smudged gray eyeshadow on her lid, leaving the edges blunt and not worrying too much about symmetry. The application was both messy and structural but also oddly intentional. The base was flawless with minimal blush, complete with a soft satin finish. The lips, of course, were coated in a bright, orange-toned red.

Perhaps one of Kelly Osbourne's most iconic looks from the early 2000s, this mega-intense, black, glittery smoky eye worn for "The Red Party" in 2003 is the very image of smudgy, grungy, messy glamour.

She didn't pull any punches with the application, packing on a swath of black eyeshadow in a circle around her eyes and layering a healthy dose of silver glitter on top. This wild eye look was coupled with a startling neon pink, overlined lip. There are methods for overlining lips for a fuller appearance, but Osbourne extended so far beyond her natural lip line that the fullness didn't translate in a believable way.

While participating in a DVD signing for "The Osbournes — The First Season" in 2003, Kelly Osbourne wore a sparkly, purple eyeshadow and smoky, gray eyeshadow look that complemented her eye color. At eye level, the look is funky, cool, and right up Osbourne's alley, but things start to go awry at the cheeks.

The generous amount of mauve blush applied all over her cheeks made her appear much older than she was at the time. Had the blush been either brighter or more neutral and applied higher on the cheekbone, the look wouldn't have aged her as drastically. Blush placement impacts a makeup look exponentially, so good technique is a must.

Just as a deeply drastic look can be shocking for viewers, a sudden shift to a whole new aesthetic can have a similarly surprising effect. Osbourne took on a whole new look at the Silver Spoon Golden Hollywood Buffet in the early 2000s, wearing a soft, ethereal makeup look instead of her usual punchy products.

She paired a soft wash of eggshell eyeshadow with a light coat of mascara and muted coral lips and cheeks. She added a bit of tasteful sparkle with a sparingly applied glitter highlight that maintained a fun, youthful element.

During a fundraising event held at the Osbournes' home in Beverly Hills, Kelly Osbourne took it upon herself to attend the party in a full 1920s-inspired look, complete with a sculpted blonde bob, long strings of pearls, and an intricately beaded flapper dress. This striking costume look was completed with an expert application of '20s-era makeup techniques, including a deep, burgundy lip, a round, midnight blue smoky eye, and thin, rounded brows. Despite being the only person in attendance dressed with a very specific theme in mind, Osbourne smiled with proud confidence, likely fully aware of how great she looked.

At the MTV Kickoff Party in 2003, Kelly Osbourne went for an unbalanced eye look, focusing more on the undereyes than the upper lid. The lower lash line was smudged with kohl liner and a neutral gray eyeshadow, and the lower lashes were coated in a heavy layer of mascara. The upper lash line was thinly lined, and her crease was slightly defined with a hint of shadow. She completed the look with a hefty amount of red blush and a glossy red lip, which gave her an almost doll-like appearance.

In a rare display of compliance with the widespread trends of the time, Kelly Osbourne strayed from bright, heavy, or dark eyeshadow and opted for a sheet of frosty gray on her eyelids for the 2003 MTV Movie Awards. She stayed true to her grungy style by applying a severe black eyeliner around the entire waterline of her eyes and completed the application with a small wing.

She traded her usual bright lipstick for a clear gloss and opted for an understated amount of blush. The look was both on par with the popular trends of the time and adequately edgy for Osbourne's taste.

Kelly Osbourne wore an updated iteration of her 2002 Teen Choice Awards look at the album release party for "The Neptunes Present...Clones" the following year. This time around, the striking eyeshadow was more densely applied and less blended. The lips had a satin finish and were applied more neatly than they were previously. The controversial color choice for the eyes maintained its startling quality, and the slight shift in technique showed how Osbourne's preferences and style had shifted over the course of a single year.

For the MTV Europe Music Awards, Kelly Osbourne chose a ghostly pale base with virtually no blush or contour, and instead of her well-known black smoky eye, she opted for a green look to shake things up.

The eyeshadow was blown out to her brows but increased in opacity the closer it came to her lash line. The look included a smoky undereye and mascara with a satin-finish, red lipstick.

Kelly Osbourne blended rock, femme fatale, and vampiric beauty for her appearance at Olympus Fashion Week in 2006. This neutral-gray cut crease, vintage eyeliner shape, and deep, blood-red lip meshed perfectly with her entire aesthetic for the night and showcased a polished, timeless (pun intended) side of her style.

The understated base makeup allowed the eyes and lips to be the stars of the look without having to compete for attention. Overall, the look was a pleasantly balanced variation of her usual style.

At the Swatch relaunch party in 2009, Kelly Osbourne tried her hand at an intense 1960s eyeliner look that featured crisp, wrap-around black liquid liner and a lower lashline filled in with white. She added emphasis to the look with the addition of a wispy strip lash glued to the drawn-on lower lash line. It was certainly graphic but featured her regularly used gray eyeshadow to draw in some of her normal style. She paired a pastel pink lip with the look that could have benefited from a deeper-toned lip liner to add structure, since the color left unlined nearly disappeared against her fair complexion.

Kelly Osbourne shocked fans with a gorgeous, skin-forward minimalist look for the opening of Odd Molly's in Los Angeles. This no-makeup makeup was fundamentally different from her history of heavy glam and proclivity for intense color and displayed her natural beauty and versatility. 

The look was complete with barely-there peachy blush and eyeshadow, her-lips-but-better lipstick, naturally filled brows, and a soft coat of mascara. Though Osbourne's classic style needs no improvement, this natural look was as refreshing as it was expertly done.

Sometimes it only takes a single element of one's makeup to make the whole look startling for viewers. Kelly Osbourne accomplished this feat by choosing the most shockingly bright lipstick for the Flaunt Magazine Anniversary Party red carpet. The shade was an impossibly bright hue of hot pink that seemed almost neon against her skin. The rest of the look was comparatively demure with grey eyeshadow and soft blush.

Kelly Osbourne leaned into the heavy bronzer and pale lip trend that took over in the 2010s. She brought the same warm, bronzy tones into a soft, smoky eyeshadow look, which gave the upper half of the makeup a harmonious quality, but unfortunately, the harmony ended there.

She paired the warmth of her eyes and base makeup with a pale pink lipstick that read like concealer in photos. Without a defining liner or contrasting color, the lips blended into her skin and nearly disappeared.

Kelly Osbourne gave fans an early 2000s throwback as she revisited her iconic black, circular smoky eye. This time, she included a few edits that displayed how her taste had developed over the course of a decade.

The application of this iteration was much more skillfully done with softly blended edges and a flattering shape that made her eyes appear bright and open despite the deep shade of the shadow. She also skipped the glitter, opting for a softer matte look, pairing the statement eye with a more demure, muted pink lip.

Sometimes, a makeup look can be jarring, not because of conscious style choices, but because of our mistakes in application or product selection. During the 2012 The Art of Elysium's Heaven Gala red carpet, Kelly Osbourne or her makeup artist made the mistake of choosing a foundation shade that was much too yellow for her complexion, and this was very evident in the photos from the night.

For the premiere of "The Hunger Games," Kelly Osbourne wore a less successful reiteration of her iconic black smoky eye compared to the one she wore for the 2010 International Interior Designer of the Year Awards Ceremony. This time around, the black eyeshadow swallowed up her eyes, being too broadly and heavily applied.

This application made her eyes look smaller and less awake, and it appeared too drastic when compared to the softer, more rounded version. She wore a slightly brighter pink lip that remained unlined and insufficiently structured.

The drastic nature of one's makeup can be rooted in the overapplication of one product or another, and this is not exclusive to color products like blush, eyeshadow, or lipstick. A product like setting powder can also greatly affect the outcome of one's overall look, as was the case for Kelly Osbourne's makeup at Logo TV's NewNowNext Awards in 2012. Her overpowdered complexion was flat and chalky on the red carpet, making her face appear mask-like and heavy despite the relatively understated eyeshadow and lips.

Instead of heavy eyes and equally heavy lips, Kelly Osbourne went for heavy blush and distracting lips for the Kreiss 75th Anniversary Celebration in 2012. Osbourne is no stranger to too much blush, and the heavy-handed application of this rosy hue is another example of her proclivity for laying this particular product on thick. What makes this look all the more theatrical is the addition of the metallic purple lipstick, which brings a new element of visual turmoil due to the dark difference in finish.