The cutoff jean short: a longstanding symbol of deeply casual living, freedom to wear as much or little as you like, and relatively wholesome sex appeal. As all-American as apple pie (or should I say cherry? More on that later), Levi's are the obvious classic. But since rising to acceptability and consequent popularity in the late 1960s, hacked-off dungarees come in all brands, lengths, and personas, including the girl next door, bona fide bad girl, gritty rocker, modern femme fatale, and irresponsible rebel.
By 1966 and right into Woodstock three years later, everything was getting repurposed, especially old, ripped jeans.
Deena Martin, Michelle Burke, Joey Lauren Adams, and Parker Posey play tough in Dazed and Confused.
While the film came out in 1993, it famously takes place in the summer of 1976, aka prime Levi's cutoffs time. A perfect pairing with a "Seniors" sweatshirt.
Catherine Bach as Daisy Duke on The Dukes of Hazzard, 1979-1985
The origin of her itty-bitty jean shorts may have been a desire to beat the Southern heat, but the effect was a whole lot of attention. Needless to say, the nickname stuck.
Bob Weir, rhythm guitarist for the Grateful Dead, rocked short cutoff jean shorts throughout the '80s and '90s.
Lookups "Weirs" on UrbanDictionary.com and the definition reads: "a pair of very short shorts worn by a ale in the style of Grateful Dead guitarist Bobby Weir. Normally attired during the summer months and accompanied with a tank top."
Video vixen and rock-star girlfriend Bobbie Brown starred in Warrant's "Cherry Pie" video in 1990.
In her memoir Dirty Rocker Boys, Brown described the experience of filming: "I feel the heat of the stage lights on me and there's a radio playing in the background...Every eye in the room is on me, and I love it."
Drew Barrymore in Poison Ivy in 1992 (left) and on downtime during the same era
Remember the old Drew? Her style revolved around an explosion of slightly gelled blonde curls, piled-on silver trinkets, a downturned mouth, and of course, cutoffs.
Cindy Crawford in a Pepsi commercial in 1992
At Crawford's arguable peak, she exuded American-bombshell cool. And she made soda look sexy.
Chloé Spring 2000 runway show
Call it the success of shock value. There's something particularly jarring about spotting a pair of tush-revealing cutoffs on a reputable runway, but that was part of the gutsy brilliance of Stella McCartney's reign at Chloé.
Gisele Bündchen, featured in the July/August 2008 issue of V Magazine
Few could make overtly tacky, shredded-to-bits, butt cleavage-spotlighting, and thoroughly Euro-trashed shorts look chic, but, well, it's Gisele.