Tom Ford Has Worn Jeans and a Cowboy Hat (Recently) The early #2000s trend of wearing dresses over jeans was a popular #y2k era look, often featuring a long dress, like a babydoll or slip dress, layered over flared or skinny jeans. 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear Project Alabama 2000s Incredible Hand Crafted Faces Dress, Rare THE WAY WE WORE How Celebrities Wore The Low Rise Jeans Trend In The Early 2000s