From trashy to classy
Madonna
Trash:

This former cheerleader turned pop icon did not make her claim to fame on grace and charm. It was a combination of her never-ending obsession to 'make it' and her media-savvy ability to create trends that catapulted the Material Girl into the limelight. Her scantily clad 'like a virgin' look went straight from MTV to high streets across the globe. Push-up bras, lace gloves, mesh shirts, micro stretch skirts and hair bows found themselves on teens worldwide. The '80s brought her countless hits and the ability to make anything trendy. But between her tumultuous marriage to Sean Penn and her sagging acting career, she struggled to prove herself as a real artist. Her album Erotica and her controversial coffee table book Sex in the '90s also made fans a little nervous.
Class:

Leave it to Madonna to emerge from it all unscathed. Somehow she manages to constantly reinvent herself - and to do so with such style that it's hard not look forward to seeing what she'll do next. Whether it's a Dolce e Gabbana vintage glittery cowboy suit or a punk-inspired plaid mini skirt, this mum of two knows how to work it.
Brad Pitt
Trash:

Brad Pitt- internationally considered one of the sexiest men alive - wasn't exactly born the stylish guy we loved in Ocean's Eleven. Brad (or William Bradley Pitt) made his start when he lied to his parents about going to college and headed to California to become an actor. His first job was dressing as a street corner chicken for fast food outlet El Pollo Loco. His next job was driving strippers to work in a limo. Soon he was getting small parts on Dallas, Growing Pains and Head of the Class. Finally he played the stud who stole Geena Davis's heart and money in Thelma and Louise. He was hot then, but a little on the grungy side. His wardrobe consisted of dirty jeans and T-shirts.
Class:

By 1998 Brad was dating Jennifer Aniston and sporting a little more style (which, of course, didn't stop him from posing for Rolling Stone magazine in a dress). It was Jennifer, however, who wore the dress to their wedding in 2000. And Brad's level of sophistication has only improved since they married - when he's not practicing the grunge look for film roles, of course.
Courtney Love
Trash:

Although Courtney was a musician in her own right as the lead singer for Hole, she became famous as the grungy, chubby wife of Nirvana's lead singer Kurt Cobain. What few people know about this celeb is that she started off as a struggling stripper who had a hard time finding work because she was too fat. She moved onto acting with a small role in Sid and Nancy, but she almost gave up on it because of pimples. 'I just couldn't pull it off. I'd get zits,' she says. However, she didn't let a few minor setbacks (and acne) stop her from making it. In 1992, at the height of her fashion grunginess, she married Cobain and gave birth to Francis Bean shortly after.
Class:

After the death of Cobain in 1994, Love took time to get herself together. In 1996 she re-emerged with an entirely new look. The former fashionless rocker with smeared lipstick and ratty hair now sported a flaxen blonde bob and looked 30 pounds lighter. She turned in her vintage baby doll dresses for Versace couture gowns. The full turnaround was evident when Love was nominated for a Golden Globe for her performance as the bisexual junkie stripper Althea Leisure in The People vs. Larry Flynt. She continues to make waves for her sense of fashion, but no one can deny the amazing transformation Love has made.
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