Kriss Kross circa 1991-92 (notice the backwards jeans)
In the mid/late 90's no rapper alive would want to be caught wearing skinny jeans. Or even a tight t-shirt for that matter. As a rule of thumb, if it isn't baggy then it ain't no good. So who were the originators and how did "the baggy style" come about?
Although in most photos of this 1989 album, Vanilla Ice appears to have super baggy MC Hammer style pants on, this low contrast version shows that it's just a shadow.
Although clothes were becoming baggier in general during the early 90s and late 80s, it's probably Kriss Kross who showcased the style the most. The two Atlanta rappers, who were 12 & 13 years old at the time, made the style complete from head-to-toe.
On this album cover from 1989, it's clear that Will Smith & Jazzy Jeff are wearing some legit super baggy pants. Cutting edge fashion.
Certainly there are many examples of the baggy style prior to Kriss Kross, one early example being the dou DJ Jazzy Jeff & The Fresh Prince on the cover of 1989's ...And In This Corner LP. And maybe most famously, MC Hammer in his "U Can't Touch This" music video from 1990.
After Kriss Kross broke in 1992, practically everyone in Hip-Hop started rocking the baggy style to the fullest. But how did this style originate? Actually there is an answer to this...
When dudes in the hood would go to the mall to buy a new outfit, they would often find that the XXLs and 3XLs were on SALE! From football jerseys to jeans, these big sizes were harder to sell and would very often be heavily discounted. So these dudes started thinking, these are great outfits and I can save money.
Cam'ron and Dipset showcasing the standard Hip-Hop baggy style of the early 2000s
As with Hip-Hop in general, the style is often to just emphasize what's already hot and just amp it up to the max. The baggier style of clothes was already the fashion in the 90's, but Hip-Hop took it to a whole other level. Every piece of clothing was as baggy as can be: huge t-shirt, huge hoodie, massive jeans and a big jacket. Capped off with some dope footwear (sneakers or boots) and a piece of headgear (snapback cap or beanie).
Even the ladies were down with baggy style - Check out this dope photo of Xscape
For those of us who lived during those days, we never thought the baggy style would go away. And indeed it lasted from about 1992 until 2010 roughly calculated. Then around 2012 the style took an ugly turn and became super skinny and weird. You know what it was. Luckily it looks like this trend has died and "normal" jeans are back in style and it even appears that the super baggy style of the 90's is making a comeback.