(Photo: Laurent Hamels/Getty Images)

1964
French denim enthusiast François Girbaud adds stones to his washing machine; his jeans emerge feeling softer and lighter. He later claims to have been the first to stonewash denim.

(Photo: McCoy Cox/Rex USA)

1980s
Ronald Reagan often sports a cowboy hat and broken-in jeans at Camp David. His technique for softening crispy new pairs: wearing them while swimming a few laps in the pool, followed by an air-dry.

1984
Bruce Springsteen’s Born in the U.S.A. hits No. 1. The album’s cover zooms in on the singer’s tattered denim backside, which is simultaneously patriotic and hot.

(Photo: Steve Azzara/Corbis)

1999
Before filming a video for the song “Heartbreaker,” Mariah Carey cuts the waistband off her denim so that the pants fit more comfortably. The increased midriff exposure is, of course, just a side benefit.

(Photo: Lloyd Francis Jr/AP)

2001
The world’s oldest known pair of jeans—made by Levi’s in the 1880s and discovered in a Nevada mining town in 1998—are bought at auction (by Levi Strauss & Co.) for $46,530.

(Photo: Steve Wood/Rex USA)

2001
Junya Watanabe devotes his spring 2002 collection to denim’s re-creation, torturing hundreds of yards of fabric and then sewing them into ragged dresses.

(Photo: Nataly Levich)

2003
Jean Shop in New York offers shoppers customized distressing for the first time.

(Photo: Splash News)

January 3, 2004
In Las Vegas, Britney Spears marries her first husband, Jason Alexander. She wears frayed jeans, accented with a white garter.

(Photo: Focus Films/Everett Collection)

2005
In Brokeback Mountain, Ennis del Mar’s repressed love has one outlet: one of his lover Jack Twist’s denim shirts, hidden inside one of his own.

2007
Bright Eyes releases Cassadaga, in which singer Conor Oberst moans, “Now the sky is a torn-up denim,” on the song “Classic Cars.”

(Photo: Courtesy of Diesel)

Spring 2008
Diesel produces Viker 8RD, its most distressed look to date. The jeans are slashed and then sewn back together. They retail for $390.

Related:

• Articles by Kendall Herbst
• Table of Contents: Jun 2, 2008 issue of New York | Subscribe!