While most can agree that they once had a rough styling phase (middle school, high school , those experimental college years), there are few who can say that they have come as far as Kelly Osbourne. The “Princess of Darkness” used to channel that in a much more literal sense, with grungy, “rock ‘n roll” outfits and a number of visible tattoos that were always paired with extreme hairdos and no smile. These days, that very same girl is a host on E!’s Fashion Police. While her styling, demeanor, and body have changed dramatically, she has maintained the characteristic sass with which she has always been associated. She now gravitates towards vintage, often pinup inspired looks that retain her personality, yet do so in a more sophisticated manner. Here is a small sampling of her style evolution over the years.
During her 2002 performance for “Top of the Pops” Kelly sported some self-decorated cargos and Vans slip-ons, a torn shirt, and equally disheveled hair.
For the 2003 MTV Music Awards, Kelly channeled her “Princess of Darkness” namesake by pairing a tiara with died black hair, severe red lips, a lingerie-inspired frock, and zip up jacket.
The 2005 Brit Awards brought out Osbourne’s girlier side as she donned a coral dress, pinup-style cardigan, and hot pink heels.
Kelly’s look for the 2006 Ray-Ban Wayfarer Uncut Sessions in London was a little more classic, with an all-black palette, Ray-Ban Wayfarer shades, timeless double-breasted coat, and statement leopard print bag.
In a lovely turn of events, Kelly sported this vintage-inspired dress and heels for the 2008 Pop Awards in London.
While out and about in Beverly Hills in 2009 Kelly kept it chic, classic, and characteristically British with a richly-colored trench, sheer tights, and Burberry scarf.
For this LA bash in 2010 Kelly found an appropriate balance between sexy, edgy, and fun, pairing a sleek leather mini dress with bubblegum pink lips, simple accessories, and a chic updo.
At the 2010 Emmy Awards, Ms. Osbourne chose a form-fitting Tony Ward dress, showcasing her amazing new body and taste in fashion.
This all-black, perfectly tailored garment was perfect for the 2011 pre-Grammy Gala.
For this year’s Emmys, Kelly chose this lavender Zac Posen gown. She paired it with black leather clutch, black diamond (literally) manicure, and bold berry-colored lips.