The VMAs has always been an opportunity to shock, awe, and make a splash in the pop cultural moment, whether you're interrupting Taylor Swift or announcing your feminist awakening. The red carpet for the show is no less of a stage for boundary-pushing fashion, stunts, and wild looks. We rounded up some of our favorite looks from years past below, including a shiny suited Lenny Kravitz, Janet Jackson rocking overalls, and Pink earing pants that defy gravity. Peep the slideshow below and time travel through some of the finest pop culture fashion flaunting you'll find anywhere, from Britney Spears to Madonna to even Donald Trump.

Steven Tyler, 1987

Run DMC, 1987

Kate Hudson in Gucci, 1998

J Lo, 1998

Poison, 1987

Lenny Kravitz and Cindy Crawford, 1993

Queen Latifah, 1990

LL Cool J, 1991

Magic Johnson and Cindy Crawford, 1992

Dennis Rodman, 1995

Billy Idol, 1984

Kriss Kross, 1992

Prince, performing in 1991

Michael Jackson and Lisa-Marie Presley, 1994

Alanis Morissette, 1995

The Notorious B.I.G., 1995

Naughty by Nature, 1993

Alyssa Milano, 1992

Salt N Pepa, 1994

Donald Trump, 1995

Cyndi Lauper, 1984

Annie Lennox, 1992

Michael Jackson and Slash, performing in 1995

Bobby Brown, 1992

Richie Sambora and Jon Bon Jovi, 1989

En Vogue, 1992

Coolio, 1994

Mark Walhberg (then Marky Mark), 1992

Wilson Philips, 1992

George Michael, 1989

Snoop Dogg and Tupac, 1996

The Fugees, 1996

Kurt Cobain and Courtney Love with daughter Frances Bean, 1993

The Cure, 1989

Janet Jackson, 1994

TLC, 1994

Madonna, 1984

Ice-T and Diane Ortiz, 1989

Tina Turner, 1984

Brad Pitt and Christina Applegate, 1989

Pink, 2000

Aaliyah, 2000

Destiny's Child, 2000

Christina Aguilera, 2000

Britney Spears, 1999

Halle Berry, 2000

Gwen Stefani, 1998

Jay Z, 1999

Missy Elliott, 1997

Marilyn Manson, 1997

Tommy Lee and Pamela Anderson, 1999

Lil Kim, 1999

The Spice Girls, 1997

Mariah Carey, 1997

The Backstreet Boys, 1999

Justin Timberlake and Britney Spears, 2000