Cindy Crawford's Changing Looks

By Jane Asher
Feb 20, 2017 @ 7:00 am
Jon Kopaloff/FilmMagic
See the icon's transformation over the years, from young model, to gorgeous mother.
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1 of 18

1988

Ron Galella/WireImage

A baby-faced Crawford was just emerging onto the modeling scene, with covers on plenty of fashion magazines and appearances in various music videos. 

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2 of 18

1990

Ron Galella/WireImage

It was this year that Crawford was famously featured on the cover of Vogue, shot by Peter Lindbergh, alongside supermodels Helena Christensen, Naomi Campbell, Linda Evangelista, Tatjana Patitz and Christy Turlington. 

3 of 18

1992

Ron Galella/WireImage

Kaia Gerber or Cindy Crawford?

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4 of 18

1993

Ron Galella/WireImage

Crawford is the perfect example of how to do brown-hued '90s makeup right. 

5 of 18

1995

Steve Granitz/WireImage

The supermodel clearly has a thing for red dresses—who could forget her iconic red Versace number at the 1991 Oscars? 

6 of 18

1996

Ron Galella/WireImage

Here, Crawford rocks her signature voluminous blowout with a glossy dark red lip.  

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7 of 18

1998

Jeff Kravitz/FilmMagic

The model experimented with curls, giving the illusion of a shoulder-length bob. 

8 of 18

2000

Ron Galella/WireImage

Here, Crawford went sleek and straight, trying out a style with brow-grazing bangs. 

9 of 18

2001

Denise Truscello/WireImage

The supermodel wears a shag-style haircut here, and pulls it off flawlessly. 

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10 of 18

2003

Gregg DeGuire/WireImage

Is it just us, or is Crawford's hair styled à la Rachel from Friends?

11 of 18

2004

Jon Kopaloff/FilmMagic

Everything about this look is so '00s and we're loving it: the lip gloss, the peach-hued blush, and of course, the shag haircut. 

12 of 18

2005

Stefanie Keenan/Patrick McMullan

The mom-of-two rocks a dewy, glowing complexion, complete with a California tan. 

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13 of 18

2007

J.Sciulli/WireImage

Crawford stuns in a fresh-faced look, wearing minimal makeup and her hair pulled back into a low ponytail. 

14 of 18

2009

Jason Merritt/Getty

With a slight side-part and face-framing layers, Crawford looks better than ever here, wearing minimal eye makeup and a pink lip. 

15 of 18

2010

Jon Kopaloff/FilmMagic

The model took her famous locks a shade lighter, rocking a slightly blonde look here, along with her signature minimal makeup.

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16 of 18

2012

JB Lacroix/WireImage

The same year of her daughter's modeling debut with Versace Kids, Crawford returns to her brunette roots, looking just as amazing as she did 20 years before. 

17 of 18

2016

Jon Kopaloff/FilmMagic

"No matter what I do, I'm not going to look 20, or 30. I just want to look great for 50. I exercise, eat healthy, and take really good care of my skin .... It's about looking great for however old you are, regardless of what that number is," she said of the pressures of aging in Hollywood. We think she looks incredible. Keep doing you, Cindy!

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