A classic red lip paired with messy hair was a perfect combination that made Winona Ryder an it girl of the ’90s–and one half of the hottest couple.
Actor Johnny Depp and actress Winona Ryder attend the 1990 NATO/ShoWest Convention on February 8, 1990 at Bally’s Hotel and Casino in Las Vegas, Nevada. Photo by Ron Galella, Ltd./WireImage.
There’s a reason she’s one of the original supermodels. Queen of the ’90s Cindy Crawford wore a bold brow and red lip better than anyone else.
Model Cindy Crawford on August 2, 1990 at the Metropolitan Museum of the Art in New York City. Photo by Ron Galella, Ltd./WireImage.
That volume! That matte lip! Julia Roberts inspired many women of the ’90s to attempt her look. And none could pull it off quite like her.
Julia Roberts during The 47th Annual Golden Globe Awards at The Beverly Hilton Hotel in Beverly Hills, California, United States. Photo by Ron Galella, Ltd./WireImage.
Naomi Campbell is barely wearing a dress, but is certainly wearing lipstick.
Naomi Campbell during on April 11, 1994 at Hotel Macklowe in New York City, New York, United States. Photo by Ron Galella, Ltd./WireImage.
Remember piecey bangs? Gwyneth Paltrow may be trying to forget.
Actress Gwyneth Paltrow attends “A Perfect Murder” New York City Premiere on June 1, 1998 at the Sony Theatres Lincoln Square in New York City. Photo by Ron Galella, Ltd./WireImage.
Ultimate ’90s it girl Liv Tyler knew to keep her hair simple with a lip like that!
Liv Tyler attends Boathouse Rocks Benefit for AIDS on June 29, 1992 at Central Park in New York City. Photo by Ron Galella, Ltd./WireImage.
Claire Danes celebrated her role in ’90s classic “Romeo + Juliet” with a spiky updo and, of course, a red lip.
Actress Claire Danes attends the “Romeo + Juliet” Hollywood Premiere on October 27, 1996 at Mann’s Chinese Theatre in Hollywood, California. Photo by Ron Galella, Ltd./WireImage.
Rosy cheeks and glossy lips made Amber Valletta one of the most natural beauties of the decade.
Model Amber Valletta attends the 1997 Spring Fashion Week: Todd Oldham Fashion Show on October 29, 1996 at Bryant Park in New York City, New York. Photo by Ron Galella, Ltd./WireImage.
Sofia Coppola took her red lip further than any other.
Sofia Coppola attends Anna Sui Fashion Show on March 31, 1993 at the New York Public Library in New York City. Photo by Ron Galella, Ltd./WireImage.
A tan, some lip gloss, and frosted eyeshadow? Yes, that’s Cameron Diaz under all that look!
Cameron Diaz during “My Best Friend’s Wedding” New York City Premiere Party at Plaza Hotel in New York City, New York, United States. Photo by Ron Galella/WireImage.
The only thing that seems to have changed over the years is Ivanka’s lipcolor. Go back to the ’90s, baby!
Donald Trump and Ivanka Trump during Valentine’s Day And Birthday Party For Ivanka Trump at Chaos in New York City, New York, United States. Photo by Ron Galella, Ltd./WireImage.