Kelly Osbourne Is The Queen Of Dramatic Makeup Looks

Kelly Osbourne first entered the zeitgeist back in the early aughts courtesy of the MTV reality show "The Osbournes" where she shared the screen with her brother, Jack, and parents Sharon Osbourne and rock-and-roll legend Ozzy Osbourne, who died in July 2025. Kelly quickly became a household name, recognized for her foul mouth and funky sense of style. Fashion obsessives of a certain age will remember that she also co-hosted "Fashion Police" on E! alongside I-said-what-I-said Joan Rivers. Cute and curvy, Kelly had to sidestep a good amount of mean-spirited body shaming; the early 2000s were a wild time. She looks way different today, though, leaving some to speculate that Ozempic is the cause of Kelly Osbourne's complete weight-loss transformation.

Throughout the years, Kelly has maintained her aura and has been known to pop out on the red carpet and for buzzy events serving dramatic makeup looks that run the gamut. We're so used to seeing her in a full beat that Kelly Osbourne is almost unrecognizable without makeup. Oscillating between rebellious punk kid in deliberately smudgy eyeliner and 1950s girly glamour in a red lip, while hitting everything in between, Kelly knows how to have fun with it.

In 2002, the same year "The Osbournes" premiered, Kelly Osbourne showed up to the Teen Choice Awards just outside of Los Angeles in a quintessential Kelly makeup look. Leave it to her to show us why red lipstick is always a good idea. This matte version was especially luscious and the similar, but not an exactly matching, crimson eyeshadow made her intense green-gold eyes pop. The swipes of unblended blush and the "yeah, whatever" attitude really brought it all together.

The red lip color that Kelly Osbourne picked out for the Topshop LA flagship store opening in 2013 is a creamier, slightly pink version that's a perfect complement to the lavender locks that she was known for at the time. Her prominent pink blush and black eyeliner that both extend way back into her hairline really brought it all together and added a bit of edge to an otherwise conventionally pretty look.

In 2016, Kelly Osbourne attended the Art of Elysium Heaven Gala, an annual charity event. Around her eyes, she opted for ultra fluffy lashes, thick black eyeliner, and a thin flick of teal along her lower lash line that stretched into a perfect wing. And we're loving the deep plum-colored matte lips. The head-turning jewel tones felt elegant and elevated, appropriate for the event, but still offered personality à la Kelly. 

The London-born Kelly Osbourne skipped back home across the pond to attend the BRIT Awards in 2008, and her simple makeup captured our punk rock hearts. The slightly smudgy black eyeshadow and liner was the perfect contrast against her eye color, and paired with this lip color that's not quite red but not too orange: chef's kiss. We also love the barely-there stamps of blush on the apples of Kelly's cheeks and the imperfect brows that look like maybe she did them herself. And the jet-black pixie that perfectly matches the eye makeup? No notes. 

Few besides Kelly Osbourne can get away with unapologetically swiping on shimmery emerald lipstick. Kelly wore the green lip color along with her trademark heavy black liner and subtly smokey shadow when she hosted the Bella magazine spring cover party in New York City in 2017. And call us crazy, but we kind of love that the lengthy lash extensions and lip color aren't exactly pristinely placed. The whole makeup look felt '80s cool, and super fun and quirky.

Maybe you remember "Charm School," the VH1 reality show that ran from 2007 to 2009. If so, you'll also remember that mom Sharon Osbourne was the host, and for one of the show's parties in New York City, Kelly Osbourne showed up with makeup that felt like a more polished, editorial version of her 2002 Teen Choice Awards look. Featuring a sea of red by way of the all-over eyeshadow, rouge, and lip gloss, it's the definition of drama. The thinner brows, pale base, and hint of sparkle underneath her eyes tie it together.

Kelly Osbourne walked the 62nd Grammy Awards' red carpet in Los Angeles in 2020 rocking a makeup look that brought the drama but was still totally on trend for the time (before the world shut down for like two years). The warm, slightly shimmery foundation made for the perfect modern base, and the different shades of purple eyeshadow, jazzed up even more with little lavender petal appliqués, felt like classic Kelly. Shout-out to the neutral nude-pink lips that didn't distract from the rest of the look.

Back in 2002, Kelly Osbourne hit the MTV Video Music Awards red carpet in New York City rocking this makeup look that served punk rebel meets wrestler in the best way possible. We can't think of a better person to pull it off, especially in the wild Y2K era. The scarlet lip is great, as is the blush on Kelly's cheeks which looks like a natural, spotty flush. We love that the all-around yellow eyeshadow was so pigmented; it almost looks like paint. And who says eyeshadow needs to stop at the eyes, anyway?