Im 33. Baggy pants showed up while i was in highschool "Cross Colors" "JNCO". Back then the pants were baggy but you kept them pulled up like normal pants.

The last few years i have noticed that the kids have the belt area of the pants under the butt cheeks and usually they have string holding them up to a belt thats wrapped around their waste. The boxers are not underwear anymore, they are usually your last layer of defense from getting an eye full. Then they have a T-Shirt thats long enough to reach their knees. It makes them look like they have tiny little legs and a long torso.

Here is an image i found just now.. Its a joke/costume but i swear this is how the kids look.