Kelly Osbourne, From Party Girl to Fashion Sage

Kelly Osbourne is certainly no stranger to fame. In fact, it runs in the family.

Her father is Ozzy Osbourne, the lead singer of the legendary heavy metal band Black Sabbath, who recently won his second Grammy at the age of 65. Her mother is Sharon Osbourne, a host of “America’s Got Talent” and “The Talk,” as well as a former contestant on “Celebrity Apprentice.” Kelly’s younger brother, Jack, has been the producer and star of several TV programs, mostly in England, as well as the third-place finisher on “Dancing With the Stars” last season. All starred together on “The Osbournes,” which ran on MTV from 2002 (when Kelly was 15) through 2005, and on which they all gained a measure of stardom as perhaps the most endearingly dysfunctional family ever to have its own show.

What followed was perhaps predictable. Kelly, by her own admission, dabbled in prescription drugs and alcohol before going through rehab multiple times. She was briefly engaged to Luke Worrall, a model, before she reportedly caught him cheating on her with a pre-op transsexual, leading to a Twitter war between the two that delighted the tabloids. (One jab from Kelly: “What do you do when someone lies in the darkest way?”)

Her weight fluctuations were obsessively chronicled by the press, a music career started out promisingly before fizzling and she quickly developed a reputation as a party girl who hung with a questionable crowd. (She once told a reporter that her mother hired a private investigator to research the background of her first boyfriend.)

“My naughty years, I won’t lie, were 13 to 24,” Ms. Osbourne, who is now 29, said recently.

But then something less predictable happened. She grew up, cleaned up and reinvented herself as a surprisingly sophisticated fashion expert.

It is that somewhat improbable journey that led her to NBC Universal’s West Hollywood studios at 8 a.m. on a Thursday in late February, taping an edition of “Fashion Police” for the E! network. As Joan Rivers, reading off a teleprompter, made a crack about the “weird arms” on a coat worn by the model Kate Moss and Giuliana Rancic cooed over Ms. Moss’s street style (“To me, she is just it”), Ms. Osbourne, in her trademark lavender bob, casually drew the viewers’ attention to the front notch of Ms. Moss’s boot, explaining how it elongated the model’s leg and enhanced her overall proportion.

Later, as a picture of Amber Heard flashed on the screen, the actress wearing a black long-sleeved Alexandre Vauthier dress at the “Three Days to Kill” premiere, Ms. Osbourne complimented the cut of the dress but said it was “too basic” for night.

That drew an admiring “She’s growing up, isn’t she?” from Ms. Rivers.

On Sunday, when actresses glide down the Academy Awards red carpet in their fanciest togs, Ms. Osbourne will be at her usual station with Ross Mathews (a.k.a., the Tara Lipinski and Johnny Weir to Ryan Seacrest’s and Ms. Rancic’s Scott Hamilton and Sandra Bezic, for those who follow both fashion and the Olympics). They will parse the looks for E!’s “Countdown to the Red Carpet” and “Live From the Red Carpet,” a job Ms. Osbourne has held for three years.

And on this morning, her appeal to audiences was on full display, especially as she fielded questions from the small studio audience during breaks in the filming, seemingly considering no topic off limits, including whom she was dating after breaking up in December with her fiancé, Matthew Mosshart, a chef.

“Gay men,” she deadpanned. “You can’t go wrong. Seriously, between Joan and my mom pimping me out, if I’m not married by the end of the year, there’s something seriously wrong.”

To a legion of fans (she has nearly 3.6 million Twitter followers and counting), that candor is pure Osbourne.

“Kelly is unafraid to say what she thinks,” said Joanna Coles, editor in chief of Cosmopolitan, which featured Ms. Osbourne on the cover last July. “She’s having a good time, but she’s also had a difficult time. She seems at a place now where she’s comfortable with herself.”

Kelly Osbourne was born in Westminster, England, and spent much of her childhood in Buckinghamshire. With the exception of her older sister, Aimee, 30, whom she described as “very private” and who left the household at an early age, the family is close-knit. Both her parents play central figures in her life, she said. (Ms. Osbourne lives down the street from them in Beverly Hills, Calif.)

“We’re all uniquely insane,” she said, fiercely. “All the money can go, all the fame can go, and you can never take our love away from us.”

Recently, Jack, 28, received a diagnosis of multiple sclerosis, a blow Ms. Osbourne said the family was dealing with “as best as you possibly can.” She added: “He’s so brave and such a champion for M.S. He came forward when many people don’t. I could go on forever talking about how brave he is.”

Aside from attending the Gateway school in Great Missenden, where one of her earliest memories was wetting her hair like Kylie Minogue on “Neighbors” for a school picture, Ms. Osbourne traveled on a tour bus with her father. Her fashion education started with seeing “how different people dress,” she said, but her mother has supplied much of her in-depth insight.

“She knows a lot about fashion, even though sometimes she goes a little Eddie ‘Ab Fab,’ ” Ms. Osbourne said with a chortle.

Ms. Osbourne is also hungry for knowledge, reading Style.com daily as well as Jezebel, Who What Wear and international fashion sites; regularly attending fashion shows, including several at the most recent London Fashion Week; and maintaining relationships with designers like Henry Holland and Zac Posen, whom she met five years ago after a photo shoot with Mr. Posen’s boyfriend, Christopher Niquet. With Mrs. Osbourne, they went shopping at Barneys in Los Angeles a few weeks ago.

“We totally have this thing where we go to every section and we’ll say, ‘That is so overpriced for what that is’ and ‘I know where they source that fabric from’ or ‘Those zips are from France and they don’t make those anymore,’ ” Ms. Osbourne said.

Mr. Posen, who has been giving her advice on her contemporary clothing line due out this fall, said, “Kelly has come to have this incredible understanding of fashion, both the craft and the humor.”

That sense of humor has certainly served her well, particularly as her teenage growing pains were on full view to millions of viewers.

“Because she grew up on national TV, she’s very familiar to people,” Ms. Coles said of Ms. Osbourne’s appeal. “She has a resonance the way the Kardashians do — there’s the idea of the authentic self. I would say Kelly has more of that than the Kardashians because she’s not perfect.”

Ms. Osbourne is not shy about discussing the imperfections of her life. After “The Osbournes,” she moved to London where, along with landing a few hosting gigs, she partied, became addicted to pain killers and soon “lost any respect I ever had within the industry.”

At the time, Mrs. Osbourne said she was in denial about her daughter’s addiction.

“Even though in the back of my head, I kind of know it, in my heart, I don’t want to say it,” she told People magazine.

Eventually, “I didn’t want to be the person I was anymore,” Ms. Osbourne said. “The only relationship I had with anybody was the pizza delivery man and the drug dealer.”

Mrs. Osbourne moved her daughter back to Los Angeles, enrolling her in rehab once again, where at 24, the results stuck.

“I’m damn proud that I kept going back until I got it,” Ms. Osbourne said.

Righting the ship, Ms. Osbourne has since been featured on “Dancing With the Stars,” an experience that has enhanced her body image (she shed several dress sizes, she said giddily). In 2011, after a successful meeting with Ms. Rivers for a “Fashion Police” slot, she began her regular duties at E!, which have come to include the red-carpet work, sometimes with Mr. Seacrest. And unlike Mr. Seacrest, whose knowledge of fashion seems to exist only as far as asking, “Who are you wearing?,” Ms. Osbourne usually comes up with an insightful observation, as when Katy Perry showed up at the Grammys this year in a Valentino couture dress that had been shown on the Paris runway less than a week earlier.

“It’s still Katy Perry kitschy, but at the same time it’s mature,” Ms. Osbourne said. “It’s not going too far in any direction.”

The E! post has given her a base from which to build her career beyond TV, one that will soon include the clothing line and a major cosmetics collaboration.

As she spent an afternoon in a design meeting at the offices of Jupi, a company that is her partner in the contemporary line and that also works with the Kardashians on their multiple collections, Ms. Osbourne held forth on zippers, fabrics and sizing, which she will offer to retailers from 0-24. The line, whose name she was not ready to reveal, has been a decade in the making, she said, and she was nearly frothing with ideas. Specifically, she was a stickler for slimming waist panels and strategically placed darts.

“I really want women to feel good in the clothes, and we’re not going to charge a woman more just because she wears a bigger size,” she said, noting the common practice in the industry for plus-size clothing. “That’s so disrespectful.”

Also, she and her mother will release a limited-edition M.A.C. collection in June. Again, details are being kept hidden.

“Our own individual flair and style is very different,” Mrs. Osbourne said mysteriously in an email, assuring that they were both “very involved in all aspects” of the line.

The project has also been incubating for years. John Demsey, a group president at Estée Lauder who oversees M.A.C., has been keeping tabs on Ms. Osbourne ever since meeting her as a 16-year-old at her parents’ house. The two spoke of makeup, but Ms. Osbourne was deemed too young at the time.

“I didn’t even know how to put makeup on properly,” she said.

The timing now feels right, Mr. Demsey said, adding that he sees a savvy young woman “who has parlayed her reality TV fame into the real deal.”

It also does not hurt, Mr. Demsey pointed out, that she befriends all the right girls, a lot as assorted as her past hair colors. Among her pals are Taylor Swift, Kim Kardashian, Rita Ora and Lil’ Kim.

Ms. Osbourne met Ms. Swift a year ago, she said, after a magazine article wrongly claimed she called the country star “disgusting” and would “do anything for attention.” Ms. Osbourne immediately emailed Ms. Swift, and the two have built a close rapport.

“It’s really nice to be able to have a normal conversation with a young girl that gets this industry,” she said. “We talk a lot, but we don’t talk about the industry. We just have fun.”

Despite friendships with stars like Ms. Swift, Ms. Osbourne said she has never cared for cliques or the fact that in Hollywood the idea of beauty “is all backward.”

“They’re all trying to be individual, but they all want to be the same,” she said. “They all have the same ombré hair; they all have the same personal trainer, weigh the same, dress the same, use the same stylist, and I just think what makes you so different is what makes you so special.”

Ms. Osbourne said that although she has grown to like Los Angeles, she “will never feel a part of it,” perhaps in part because she seems to believe in good manners, a point that Ms. Coles seconded when she fondly recalled a thank-you note sent to her by Ms. Osbourne after she appeared on the Cosmo cover.

“I’ll never understand that about this town,” Ms. Osbourne said, before slipping on lilac shades and driving back out into the sunshine. “People think they’re just owed it when they’re not.”