The 1950s

thumb|right|Elvis wearing drainpipe jeans. In the 50s the waist was higher than on modern skinny jeans The style of pants originated in the 1950s, with popular stars such as Roy Rogers, Lone Ranger, Cisco Kid, Zorro and Gene Autry, Marilyn Monroe, and Sandra Dee wearing their pants very slim to the ankle. Skinny jeans became most notable with country music stars and with the birth of rock and roll in the 1950s, when Elvis Presley donned slim-fitting jeans and shocked the country. Skinny jeans and rock 'n' roll were inextricably linked to create the bad boy image that remains today. Skinny jeans were also worn by numerous rock bands, including The Beatles and The Rolling Stones. Drainpipe jeans (as they were then called) were popular in the punk subculture of the late 1970s, worn by many bands and scene leaders such as The Clash, Ramones, The Sex Pistols and were sold by the revolutionary shop Sex, run by Vivienne Westwood. The tight fit trousers were often customised with bondage-style zips or patches of other material, and were often worn tucked into industrial-style boots such as Dr. Martens.

The 1980s

Skinny jeans were also very popular in the 1980s, with most heavy metal bands, and in particular those in the thrash scene, such as Anthrax, Megadeth, Metallica and Slayer. This was the trend for those who didn't wear spandex, which was popular with the dominant glam metal scene at the time. They were often worn with white high-top sneakers or basket-ball shoes. By the late 1980s and early 1990s, many hair metal bands such as Poison, and Mötley Crüe to Kiss, Bon Jovi and Slaughter, ditched the spandex and wore the form fitted jeans. However with the rise of grunge and hip-hop music in the early nineties and the post thrash movement, skinny jeans quickly went out of favour although some people still wear them to have the "old school" metal appearance.

The 2000s

In the early 2000s, they became favored by Dirty Joe revival bands, most notably by The Strokes. Model Kate Moss has been credited with reintroducing the jeans to women. Among women, skinny jeans are most often worn tucked into boots or scrunched up over the wearer's footwear, and are also often paired with ballerina flats. The Libertines (particularly Carl Barat and Pete Doherty) used skinny jeans as part of their image. This was later adopted by more mainstream indie pop and indie rock acts such as Kaiser Chiefs, Kasabian, The Kooks and The Horrors, as well as comedians Russell Brand and Noel Fielding, increasing the popularity of skinny jeans amongst men. The skinny jean became very popular in Britain when Topman started producing their own. The buzz later hit America and has now become a staple item of clothing for anyone who wants that Rock 'n' Roll look. Some skateboarders prefer to wear the jeans because of their ability to stretch, thus making it easier to move around whilst skating. Skinny jeans are also now very prominent in the BMX scene resulting in greater maneuverability and less instances in which the pants are caught in the bike's moving parts. They have grown in the latter half of the 2000s to become associated with a scene and indie rock trend. They now come in colors such as red, bright blue, gray, green, and purple, other than black. The skinny jeans wear is now starting to reach the hip-hop genre such as New Boys, Kanye West and more. African and Latin Americans are beginning to wear skinny jeans.