Your favorite pop star wasn’t always decked out in the best fashion, and your favorite rapper didn’t step a foot in Bergdorf Goodman, yet they still conquered the scene with their musical ambitions. Stars like Jay-Z, Jennifer Lopez and Will Smith, all extremely popular today, went through a few crazy fashion trends that many of us have adopted. Other styles, however, we just can’t help but laugh at.

Check out your favorite celebrities before they met that wonderful stylist.



Bobby Brown, 1989

Bobby Brown in 1989. Yup that looks about right.

Jaz-O, Queen Latifah & Jay-Z, 1990

Jaz-O, Queen Latifah & Jay-Z in 1990. Rap will never be the same.

Will Smith, 1990

Will Smith was real colorful back in 1990

LL Cool J, 1989

LL Cool J's look in 1989 has been brought back from the dead, however, the gaudy jewelry never left the game.

Ricky Martin, 1990s

Ricky Martin living la vida loca in the 1990s

Mariah Carey, 1990s

Mariah Carey's cut-off jeans made their way into everyone's closet in the 1990's and brought way to the low rise jean.

Jay-Z, 1995

Jay-Z in 1995. I could see this coming back and marked up an extra $100.. courtesy of RocaWear.

Salma Hayek, 1995

Salma Hayek rocked the dark red lips which was big around 1995

Lenny Kravitz & Lisa Bonet, 1988

Lenny Kravitz & Lisa Bonet in 1988. They look about the same.

Justin Timberlake, 1998

Justin Timberlake wearing the big and baggy style in 1998

Beyoncé Knowles, 2001

Beyoncé Knowles in 2001. A Tina Knowles creation i'm sure.

Britney Spears, 2000

Britney Spears made her way to pop stardom in her body hugging outfits (2000)

Will Smith & Jada Pinkett Smith, 1997

Will Smith & Jada Pinkett Smith took matching to the extreme in 1997

Usher, 1999

Usher, where did you get the coat? (1999)

Jennifer Lopez & Ja Rule, 2001

Jennifer Lopez & Ja Rule, 2001. The bandana/towel head wrap was popular then (2001)

Damon Dash & Kanye West, 2002

Damon Dash & Kanye West in 2002. A Jersey with no shirt? Sir.

Christina Aguilera, 2000

Christina Aguilera, 2000

Alicia Keys, 2001

Alicia Keys back in 2001.