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Sade This picture has graced many a mood board thanks to Sade's flawless combination of a light chambray shirt, loose-fitting dad jeans, large go...
Sade This picture has graced many a mood board thanks to Sade's flawless combination of a light chambray shirt, loose-fitting dad jeans, large gold hoops, long braid, and a red lip to finish.
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Audrey Hepburn No one has ever balanced chic and tomboy better than Audrey Hepburn. Though she is often associated with Givenchy couture, this lo...
Audrey Hepburn No one has ever balanced chic and tomboy better than Audrey Hepburn. Though she is often associated with Givenchy couture, this look from Two For The Road — high-waisted, tapered jeans with a wide leather belt and a sweater tucked in — has been engrained in fashion history forever.
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Aaliyah '90s R&B queen Aaliayh made "sexy on top, tomboy on the bottom" a look every teenager wanted to copy, and a style designers...
Aaliyah '90s R&B queen Aaliayh made "sexy on top, tomboy on the bottom" a look every teenager wanted to copy, and a style designers still imitate.
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Britney Spears and Justin Timberlake Nothing says "young love" like couple coordination at the American Music Awards. History was made ...
Britney Spears and Justin Timberlake Nothing says "young love" like couple coordination at the American Music Awards. History was made with this photo.
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Brooke Shields This Calvin Klein Jeans ad made high-waisted, dark denim jeans into a classic silhouette that would remain popular for decades to ...
Brooke Shields This Calvin Klein Jeans ad made high-waisted, dark denim jeans into a classic silhouette that would remain popular for decades to come.
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Debbie Harry The queen of punk rock wore the Canadian tuxedo long before it was a trend.
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Cindy Crawford Nobody does all-American denim better than Cindy Crawford. From her iconic Pepsi ads to her off-duty style, she's always brought i...
Cindy Crawford Nobody does all-American denim better than Cindy Crawford. From her iconic Pepsi ads to her off-duty style, she's always brought inspiration with her retro denim looks.
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Daisy Dukes Even if Dukes of Hazzard isn't your kind of television, we're pretty sure you've seen Catherine Bach's infamous short short...
Daisy Dukes Even if Dukes of Hazzard isn't your kind of television, we're pretty sure you've seen Catherine Bach's infamous short shorts.
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Farah Fawcett The Charlie's Angels star made the super-wide-leg flared jean an instant favorite.
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Jane Birkin Jane Birkin's place in style was solidified when Hermès named a bag after her, but let's not forget about her laid-back, off-d...
Jane Birkin Jane Birkin's place in style was solidified when Hermès named a bag after her, but let's not forget about her laid-back, off-duty denim style.
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Marilyn Monroe The photo of her Seven Year Itch dress fanning up over the updraft from the subway is iconic, but she also rocked some c...
Marilyn Monroe The photo of her Seven Year Itch dress fanning up over the updraft from the subway is iconic, but she also rocked some casual outfits that we still copy today, like the boyfriend jeans she wore in The Misfits.
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Naomi Campbell Even though this look is from a show in the '90s, Naomi makes it look timeless.
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Ralph Lauren He pioneered the Polo shirt but has reinvented denim in more ways than one. And he closes all of his runway shows in a boot-cu...
Ralph Lauren He pioneered the Polo shirt but has reinvented denim in more ways than one. And he closes all of his runway shows in a boot-cut version complete with Western boots.
Photo: Getty Images/Photo: Gianni Pucci / Indigitalimages.com
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Twiggy You can't talk about fashion in the '60s without bringing up Twiggy — she was a beauty muse for tons of designers, and her laid-back, boyi...
Twiggy You can't talk about fashion in the '60s without bringing up Twiggy — she was a beauty muse for tons of designers, and her laid-back, boyish style is still emulated to this day.
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TLC When you think of a sexy way to wear denim overalls, you think of TLC. They brought a fresh flavor to classics and consistently found new way...
TLC When you think of a sexy way to wear denim overalls, you think of TLC. They brought a fresh flavor to classics and consistently found new ways to make denim their own.
Photo: Getty Images