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9.
The way I've heard it is that sagging was a way for guys in prison to show that they had a gang behind them, or that they were in charge of a large group of inmates. It was like saying "here's my ass, go ahead, TRY to rape me."
That guy wears his pants around his knees cause he knows someone's always got his back.
by Yargh April 25, 2005
 
1.
wearing ones pants around the hips so that they sag down and bunch up around the ankles. Originally, this was a prison thing that signified that you were another prisoner's property, ie bitch. Punks were forced to wear their pants this way so it would be easier for their masters to pull their pants down and butt-fuck them. Somehow this became a 1990's fashion trend. I learned this from watching a TV special on prison life. The inmate who related the story was an elderly black gentleman who had been sentenced to life in prison and had been there for over fifty years. He marveled how such a mark of shame became a fashion statement. He said that younger inmates don't believe him when he tells them but swears it's the truth. I believed him. I also think they should let him out already, he's like 80 and I don't think he represents a threat to society.
Look at any wanna-be gangster (wankster) How the hell are you supposed to run from cops with your pants around your hips and your shoes unlaced anyway. If any of these little punk-asses actually did anything bad enough to get them thrown in the slammer they would no doubt shortly find out exactly what saggy pants are good for.
by Spanky McSpunk April 15, 2003
 
2.
Wearing your pants below your waist. It originally meant you were gay in prison (much research into finding and confirming that) but somehow became fashionable. It did not originally mean anything about a gang, which is an extremely common misconception. There is nothing cool about wearing your pants low.
Look at that faggot sagging his jeans almost as low as his knees.
by SaggingIsForGayCriminals February 19, 2012
 
3.
Hip-hop and gangster cultural fashion: Wearing one's pants below the level of the waist, sometimes below the level of the buttocks, with one's boxer shorts showing. The style may date back to around 1989.

The origin of this originally young, urban, black style is unknown. A commonly accepted origin theory was that is was an outgrowth of prisons, where inmates' clothing was often too large and sometimes no belts were allowed.

It may be related to skateboard/snowboard fashion.

At least one scholar thinks there is a tie-in with African culture.

There is also some evidence that a male showing his underwear-covered buttocks in prison was, at one point, linked to a desire for sex, or a mark that a prisoner was "owned" by another prisoner, sexually. Whether this kind of showing one's buttocks has any relation to sagging is unclear.

Some areas have begun to outlaw this style recently (2011). Apparently the objection is the amount of underwear shown.
He was sagging, hitching up his pants, shuffling down the street, with a swagger. He was really busting a major sag.
by Awed2 June 20, 2011
 
4.
Sagging refers to the wearing of pants in a way that exposes the top portion of the underwear. Exposing more than the top portion of the underwear is considered a poor execution of the style. It is also inappropriate “to sag” when wearing briefs. Designer boxers are required. A belt is also required to prevent the pants from sagging beyond the upper portion of the back side. To sag with the entire back side exposed is considered poor form. The idea is to provide brief glimpses of the designer boxers as opposed to prolonged exposure.

Many myths and lies about sagging have been promoted to discourage the style. Sagging started around 1989 as a way for African American men to avoid what was perceived in the African American community as a homosexual look favored by white men in the mid to late 80s. The manufactures of the most popular brands such as Jordache and Levis did not manufacture jeans that were cut to fit the African American shape. In short, most if not all jeans would fit African Americans very, very tight and to the point that is was uncomfortable. White people tended to favor the tight fit while African Americans shunned it. To make the jeans fit in way that was more acceptable to African Americans, teen age kids and hip hop stars would buy there jeans two or three sizes too big. This started the trend of “baggy clothes.” Sagging became popular as well as a way to avoid the “homosexual look” of tight jeans. Also because the jeans were two or three sizes too big.
I have be sagging at all times...can't be walkin around lookin like Axel Rose.

I will always be sagging. Let them whiteboys wear them nuthuggers.
by Old School 235 June 18, 2013
 
5.
straiming of the ship which tends to make the middle portion lower than the bow and stern
the vessel (almost large ships) is sagging and hogging on high seas
by waterkantwilli February 20, 2006
 
6.
wearing ones pants below the waist to make pants baggier. This is seen as a "cool" way to wear pants, as seen by the number of rappers, skaters, rock stars, etc. that wear them. Usually a belt is not worn to reinforce sagging.
I was walking down the street, and my pants were sagging, so i had to pull them up every 3 seconds.
by Anonymous September 06, 2003
 
7.
Sagging – something wanna be rock kids / black people seem to be doing i.e. wearing your “pants” around your ass. It also happens to the name given to some rather hot video clips posted on the net. Try tube surfing to find it.
I watch sagging online - to get myself off
by Andy the great May 18, 2006