Ashley Tisdale's 2000s Outfits 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. Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Jessica Alba Just Reminded Us About This Inescapable Denim Trend From the 2000s Tom Ford Has Worn Jeans and a Cowboy Hat (Recently) 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear