In 1960, actress (and fashion icon) Marilyn Monroe cuffed her fitted high-waisted jeans on the set of The Misfits.
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Jane Birkin, 1973
Back in 1973, model Jane Birkin posed on a boat in flared denim. During the era, flared high-waisted jeans were worn on models and actors alike. Birkin was also shown wearing another major trend of the decade — unfinished hems.
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Farrah Fawcett, 1976
Actor Farrah Fawcett made riding a skateboard look chic with her on-trend bell-bottoms and Nike Cortez sneakers while on set for Charlie's Angels in 1976.
Princess Diana 1988
Princess Diana's jeans and boots combo at the Guards Polo Club back in 1988 is still a popular look today, and with good reason.
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Cindy Crawford, 1992
Supermodel Cindy Crawford wore a pair of '90s mom jeans for an off-duty look at the airport in London.
Kate Moss, 1996
Model Kate Moss promoted a pair of slouchy straight-leg Calvin Klein Jeans in 1996 at a Macy's store.
Jennifer Anniston, 1998
For the Six Days & Seven Nights premiere in 1998, Jennifer Anniston rocked a pair of medium-wash baggy jeans, which the actor cuffed at the bottoms.
Jennifer Lopez, 2000
Welcome to the early 2000s, where the denim went as low as it could go. This was proven by J.Lo's bedazzled low-rise denim look at the VMAs in 2000, which happens to be one of the star's most talked-about fashion moments.
Naomi Campbell, 2001
For Michael Jackson's 30th anniversary celebration, model Naomi Campbell arrived baring her midriff with low-rise denim and a cropped blouse. Very on-point for the early 2000s, no?
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Britney Spears and Justin Timberlake, 2001
The prize for the most iconic couples denim moment goes to — drumroll, please — Britney Spears and Justin Timberlake at the VMAs in 2001.
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While leaving her hotel in London during a trip in 2012, Rihanna was pictured wearing a full denim ensemble consisting of a button-up top, itty bitty shorts detailed with silver spikes, and a jean jacket tied around her waist.
Kerry Washington, 2013
New York-based label 3x1's fringe jeans were the It bottoms of the mid-2000s. Kerry Washington sported the coveted jeans while arriving at the Jimmy Kimmel show in 2016.
Selena Gomez, 2016.
At the WE Day California event in 2016, Selena Gomez arrived in Vetements' Blue High-Rise Crop reworked Levi’s from the brand's Fall/Winter 2015 collection.
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Megan Markle 2017
Princess Diana wasn't the only royal to be pictured in a pair of relaxed jeans. Alongside the prince, Megan Markle opted for light wash denim with rips from Mother Denim at the 2017 Invictus Games in Toronto.
Bella Hadid, 2020
As of late, straight-leg jeans have been coming back into the fashion scene thanks to brands like Frame and Acne Studios. Bella Hadid paired her bottoms with a cool oversized denim jacket while out and about in New York.