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look book
September 23, 2014

See Supermodel Cindy Crawford’s Most Iconic Looks

By Leah Rodriguez

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Photo: Ron Galella

Throughout the ‘90s, no other American model was as omnipresent as Cindy Crawford: She ruled the catwalk, starred in dozens of swimsuit spreads, and even hosted MTV’s House of Style. Known to draw attention to her lips with a red pout, she mastered the bouncy hair of the ‘80s, wore furry gloves and berets in the ‘90s, but — no matter the decade — always embraced curve-hugging dresses. Click ahead to see her best outfits throughout the ages — including guest appearances by fellow super Claudia Schiffer and former beau Richard Gere.

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1 / 84 Photos
January 10. 2017  Where: At the Marie Claire Image Maker Awards. What: Dress by Balmain. Photo: Frazer Harrison/Getty Images
June 27, 2013 Where: With Rande Gerber at the opening of "Helmut Newton: White Women - Sleepless Nights - Big Nudes." Photo: Mark Sull... June 27, 2013 Where: With Rande Gerber at the opening of "Helmut Newton: White Women - Sleepless Nights - Big Nudes." Photo: Mark Sullivan/2013 Getty Images
May 15, 2013 Where: At The Great Gatsby premiere and opening ceremony during the Cannes Film Festival. Photo: Ian Gavan/2013 Getty Images
April 18, 2013 Where: At the Rock and Roll Hall of Fame induction ceremony in Los Angeles, California. Photo: Jason Merritt/2013 Getty Images
March 10, 2013 Where: With Rande Gerber at the John Varvatos tenth annual Stuart House benefit presented by Chrysler in Los Angeles, California. ... March 10, 2013 Where: With Rande Gerber at the John Varvatos tenth annual Stuart House benefit presented by Chrysler in Los Angeles, California. Photo: Frederick M. Brown/2013 Getty Images
May 22, 2012 Where: At the launch of Caliche Rum hosted by Rande Gerber and Roberto Serralles in New York City. Photo: Jim Spellman/2012 Jim Spe... May 22, 2012 Where: At the launch of Caliche Rum hosted by Rande Gerber and Roberto Serralles in New York City. Photo: Jim Spellman/2012 Jim Spellman
May 2, 2012 Where: At the International Press Academy of Beverly Hills Honors Brian Edwards in West Hollywood, California. Photo: JB Lacroix/201... May 2, 2012 Where: At the International Press Academy of Beverly Hills Honors Brian Edwards in West Hollywood, California. Photo: JB Lacroix/2012 JB Lacroix
March 11, 2012 Where: With Rande Gerber at the John Varvatos Stuart House benefit. Photo: Frederick M. Brown/2012 Getty Images
February 8, 2012 Where: At the amfAR New York Gala to kick off fall 2012 Fashion Week in New York City. Photo: Jemal Countess/2012 Getty Images
November 15, 2011 Where: At the premiere of The Descendants in Beverly Hills, California. Photo: Alberto E. Rodriguez/2011 Getty Images
November 8, 2011 Where: At the OMEGA Watches party in Buenos Aires, Argentina. Photo: Lalo Yasky/2011 Lalo Yasky
September 21, 2011 Where: At the premiere of Mexico: The Royal Tour in Los Angeles, California. Photo: Christopher Polk/2011 Getty Images
August 31, 2011 Where: At The Ides of March premiere in Venice, Italy. Photo: Vittorio Zunino Celotto/2011 Getty Images
April 29, 2011 Where: At the Race to Erase MS Gala in Los Angeles, California. Photo: Frederick M. Brown/2011 Getty Images
March 22, 2011 Where: At the premiere of the HBO documentary His Way in Hollywood, California. Photo: Frazer Harrison/2011 Getty Images
October 25, 2010 Where: On the set of EXTRA in Los Angeles, California. Photo: Michael Caulfield/2010 Getty Images
March 22, 2010 Where: At DIFFA's Dining by Design in New York City. Photo: Astrid Stawiarz/2010 Getty Images
March 2, 2010 Where: At the JCPenney Discover Spring Style event in New York City. Photo: Neilson Barnard/2010 Getty Images
December 10, 2009 Where: At the UNICEF Ball in Beverly Hills, California. Photo: Jason Merritt/2009 Getty Images
November 30, 2009 Where: At the premiere of Up in the Air. Photo: Jason Merritt/2009 Getty Images
November 5, 2009 Where: With Rande Gerber at the premiere of A Single Man in Los Angeles, California. Photo: Kevin Winter/2009 Getty Images
October 15, 2009 Where: At the launch party of the OMEGA 2009 Constellation Collection in London, England. Photo: Ian Gavan/2009 Getty Images
October 15, 2009 Where: At the opening of the OMEGA Boutique at the Village in London, England. Photo: Samir Hussein/2009 Getty Images
October 14, 2009 Where: At the opening gala premiere after-party of Fantastic Mr. Fox during the the Times BFI London Film Festival. Photo: Dave... October 14, 2009 Where: At the opening gala premiere after-party of Fantastic Mr. Fox during the the Times BFI London Film Festival. Photo: Dave Hogan/2009 Dave Hogan
September 9, 2009 Where: At the JCPenney launch party for Cindy Crawford Style in New York City. Photo: Theo Wargo/2009 Getty Images
June 18, 2009 Where: Presenting the new Remington hair straightener in Buenos Aires, Argentina. Photo: Lalo Yasky/2009 Lalo Yasky
May 4, 2009 Where: At "The Model as Muse: Embodying Fashion" Costume Institute Gala at the Metropolitan Museum of Art in New York City.... May 4, 2009 Where: At "The Model as Muse: Embodying Fashion" Costume Institute Gala at the Metropolitan Museum of Art in New York City. Photo: Larry Busacca/2009 Getty Images
September 20, 2008 Where: At the Michigan Avenue magazine launch party in Chicago, Illinois. Photo: Lyle A. Waisman/2008 Lyle A. Waisman
April 26, 2008 Where: At the GLAAD Media Awards in Hollywood, California. Photo: Neilson Barnard/2008 Getty Images
March 31, 2008 Where: At the premiere of Leatherheads in Hollywood, California.       Photo: Michael Buckner/2008 Getty Images
March 9, 2008 Where: At the John Varvatos Stuart House benefit at the John Varvatos boutique on March 9, 2008, in West Hollywood California. Pho... March 9, 2008 Where: At the John Varvatos Stuart House benefit at the John Varvatos boutique on March 9, 2008, in West Hollywood California. Photo: Tiffany Rose/2008 Getty Images Tiffany Rose
February 10, 2008 Where: At the Warner Music Group GRAMMY Awards after-party held in Los Angeles, California. Photo: David Livingston/2008 Getty... February 10, 2008 Where: At the Warner Music Group GRAMMY Awards after-party held in Los Angeles, California. Photo: David Livingston/2008 Getty Images
February 1, 2008 Where: At MAXIM magazine kicks off Super Bowl weekend. Photo: Michael Buckner/2008 Getty Images
October 28, 2007 Where: At the Murakami Gala at MOCA hosted with Louis Vuitton event honoring fashion designer Marc Jacobs in Los Angeles, Califo... October 28, 2007 Where: At the Murakami Gala at MOCA hosted with Louis Vuitton event honoring fashion designer Marc Jacobs in Los Angeles, California. Photo: Mark Davis/2007 Getty Images
September 18, 2007 Where: At the 30 Days of Fashion event hosted by Hearst Magazines in New York City. Photo: Scott Wintrow/2007 Getty Images
September 15, 2007 Where: At the Stella McCartney and Tastybaby 2008 collection preview event at the Stella McCartney store in West Hollywood, Ca... September 15, 2007 Where: At the Stella McCartney and Tastybaby 2008 collection preview event at the Stella McCartney store in West Hollywood, California. Photo: Frazer Harrison/2007 Getty Images
June 5, 2007 Where: At the U.S. premiere of Ocean's Thirteen in Hollywood, California.      Photo: GABRIEL BOUYS/2007 AFP
April 18, 2007 Where: At the opening of the Oscar de la Renta boutique in Los Angeles, California. Photo: Frazer Harrison/2007 Getty Images
February 8, 2007 Where: At the Rodeo Drive Walk of Style Awards in Beverly Hills, California. Photo: GABRIEL BOUYS/2007 AFP
October 13, 2006 Where: With Rande Gerber at the American Cinematheque Award honoring George Clooney in Beverly Hills, California. Photo: Mark M... October 13, 2006 Where: With Rande Gerber at the American Cinematheque Award honoring George Clooney in Beverly Hills, California. Photo: Mark Mainz/2006 Getty Images
May 11, 2006 Where: At the U.S. launch of Roberto Cavalli Vodka. Photo: Kevin Winter/2006 Getty Images
February 7, 2006 Where: With Rande Gerber at the Versace store reopening party in New York City. Photo: Mat Szwajkos/2006 Getty Images
February 7, 2006 Where: At a launch party for the new Stephen Knoll New York hair-care collection in New York City. Photo: Evan Agostini/2006 Ge... February 7, 2006 Where: At a launch party for the new Stephen Knoll New York hair-care collection in New York City. Photo: Evan Agostini/2006 Getty Images
September 20, 2005 Where: At the W Hotel fund-raiser for Hurricane Katrina. Photo: Marsaili Mcgrath/2005 Getty Images
May 1, 2005 Where: At the Runway for Life Benefiting St. Jude Children's Research Hospital and Celebrating the DVD release of NATIONAL TREASURE i... May 1, 2005 Where: At the Runway for Life Benefiting St. Jude Children's Research Hospital and Celebrating the DVD release of NATIONAL TREASURE in Los Angeles, California. Photo: Mark Mainz/2005 Getty Images
March 7, 2005 Where: At a private dinner for the new OMEGA jewelry collection in Madrid, Spain. Photo: Carlos Alvarez/2005 Getty Images
February 15, 2005 Where: At the opening of Roberto Cavalli's new Rodeo Drive boutique in Beverly Hills, California. Photo: Amanda Edwards/2005 G... February 15, 2005 Where: At the opening of Roberto Cavalli's new Rodeo Drive boutique in Beverly Hills, California. Photo: Amanda Edwards/2005 Getty Images
December 8, 2004 Where: With Rande Gerber at the Ocean's Twelve Los Angeles premiere. Photo: SGranitz
May 11, 2004 Where: At the City of Hope Spirit of Life luncheon in New York City. Photo: Peter Kramer/2004 Getty Images
February 4, 2004 Where: With Rande Gerber at the Time Warner Center grand-opening celebration in New York City. Photo: Arnaldo Magnani/2004 Arna... February 4, 2004 Where: With Rande Gerber at the Time Warner Center grand-opening celebration in New York City. Photo: Arnaldo Magnani/2004 Arnaldo Magnani
October 9, 2003 Where: At the Condé Nast Traveler Readers' Choice Awards in New York City. Photo: Evan Agostini/2003 Getty Images
September 23, 2003 Where: At the launch party for the new Cindy Crawford OMEGA campaign. Photo: Dave Benett/2003 Dave Benett
September 25, 2002 Where: At the Dream Foundation to Host Star-Studded Extravaganza Fundraiser - "Le Cabaret Des Reves" in Los Angeles,... September 25, 2002 Where: At the Dream Foundation to Host Star-Studded Extravaganza Fundraiser - "Le Cabaret Des Reves" in Los Angeles, California. Photo: Chris Polk
May 21, 2002 Where: Co-hosting private party to celebrate the opening of the Martin Katz LTD. jewelry salon in Beverly Hills, California. Photo:... May 21, 2002 Where: Co-hosting private party to celebrate the opening of the Martin Katz LTD. jewelry salon in Beverly Hills, California. Photo: Donato Sardella
December 5, 2001 Where: At the world premiere of Ocean's Eleven. Photo: SGranitz
March 1, 2001 Where: With Rande Gerber at the St. Jude Hollywood Gala. Photo: Jean-Paul Aussenard
March 4, 1999 Where: At the St. Jude Children's Hospital Benefit Gala in Beverly Hills, California. Photo: Ron Galella, Ltd./1999 Ron Galella, Ltd.
September 14, 1998 Where: At Christie Hefner Hosts a Party for Cindy Crawford in New York City. Photo: Ron Galella
July 14, 1998 Where: At the Revlon and VH1 Present "Lilith Rocks for Women's Health" to Celebrate Lilith Fair and Special Donation to t... July 14, 1998 Where: At the Revlon and VH1 Present "Lilith Rocks for Women's Health" to Celebrate Lilith Fair and Special Donation to the National Women's Cancer Research Alliance in New York City. Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
June 17, 1998 Where: At the Out of Sight Los Angeles premiere. Photo: SGranitz
June 5, 1997 Where: At the California Fashion Industry Friends of AIDS Project Los Angeles Fashion Show and Dinner to Honor Tom Ford.  Phot... June 5, 1997 Where: At the California Fashion Industry Friends of AIDS Project Los Angeles Fashion Show and Dinner to Honor Tom Ford.  Photo: Ron Galella, Ltd./1997 Ron Galella, Ltd.
June 10, 1995 Where: At the MTV Movie Awards. Photo: Ron Galella, Ltd./1995 Ron Galella, Ltd.
September 17, 1994 Where: With Jon Bon Jovi during a video shoot in Los Angeles, California. Photo: Neal Preston/© Corbis. All Rights Reserved.
Circa 1994 Where: With Richard Gere. Photo: Mitchell Gerber/© Corbis. All Rights Reserved.
October 26, 1993 Where: Departing for New York City at Los Angeles International Airport in Los Angeles, California. Photo: Ron Galella, Ltd./19... October 26, 1993 Where: Departing for New York City at Los Angeles International Airport in Los Angeles, California. Photo: Ron Galella, Ltd./1993 Ron Galella, Ltd.
September 29, 1993 Where: With Cindy Crawford, Joan Walz, Claudia Schiffer, and Veronica Webb in New York City.       Photo:... September 29, 1993 Where: With Cindy Crawford, Joan Walz, Claudia Schiffer, and Veronica Webb in New York City.       Photo: Jim Smeal
September 2, 1993 Where: At a reception for the MTV Video Music Awards in Los Angeles, California. Photo: Frank Trapper/© Corbis. All Rights Re... September 2, 1993 Where: At a reception for the MTV Video Music Awards in Los Angeles, California. Photo: Frank Trapper/© Corbis. All Rights Reserved.
July 11, 1993 Where: At the Video Software Dealers Association Convention and Expo. Photo: Ron Galella, Ltd./1993 Ron Galella, Ltd.
December 1, 1992 Where: With Richard Gere at a World AIDS Day lunch. Photo: Rick Maiman/© Corbis. All Rights Reserved.
September 14, 1992 Where: With Claudia Schiffer during Revlon's Unforgettable Woman Contest in New York City. Photo: Ron Galella
September 9, 1992 Where: At the MTV Video Music Awards. Photo: Ron Galella, Ltd./1992 Ron Galella, Ltd.
August 30, 1992 Where: At the Emmy Awards. Photo: Ron Galella, Ltd.
April 2, 1992 Where: At Vogue Magazine's 100th Anniversary Celebration in New York City. Photo: Ron Galella, Ltd./1992 Ron Galella, Ltd.
March 31, 1992 Where: With Richard Gere at the Academy Awards. Photo: Art Streiber/© Corbis. All Rights Reserved.
May 1, 1991 Where: Interviewing photographer Francesco Scavullo for MTV during the Love Ball, a fund-raiser for AIDS research in New York City. ... May 1, 1991 Where: Interviewing photographer Francesco Scavullo for MTV during the Love Ball, a fund-raiser for AIDS research in New York City. Photo: Mark Peterson/© Corbis. All Rights Reserved.
Circa 1991 Where: With Richard Gere at the Moving Picture Ball honoring Martin Scorsese in Los Angeles, California. Photo: Frank Trapper/© Corbi... Circa 1991 Where: With Richard Gere at the Moving Picture Ball honoring Martin Scorsese in Los Angeles, California. Photo: Frank Trapper/© Corbis. All Rights Reserved.
February 13, 1991  Where: At the California Industry Friends of AIDS Project Los Angeles Fashion Show and Dinner to Honor Gianni Versace in Los A... February 13, 1991  Where: At the California Industry Friends of AIDS Project Los Angeles Fashion Show and Dinner to Honor Gianni Versace in Los Angeles, California.   Photo: Ron Galella, Ltd./1991 Ron Galella, Ltd.
August 23, 1990 Where: At a press conference to announce her association with JH Collectibles to launch a sportwear line in New York City. Photo... August 23, 1990 Where: At a press conference to announce her association with JH Collectibles to launch a sportwear line in New York City. Photo: Ron Galella, Ltd./1990 Ron Galella, Ltd.
August 2, 1990 Where: At the Metropolitan Museum of Art in New York City. Photo: Ron Galella
March 13, 1990 Where: At Art Pro Choice. Photo: Ron Galella
November 17, 1989 Where: Promoting her 1990 calendar in New York City. Photo: Ron Galella
May 10, 1989 Where: At the Love Ball to Benefit the Design Industries Foundation for AIDS in New York City. Photo: Ron Galella/1989 Ron Galella
March 1989  Photo: Wayne Maser/© Corbis. All Rights Reserved.
April 5, 1988 Where: At the Hooray for Hollywood AIDS Benefit. Photo: Ron Galella
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