The Y2K Dress Over Pants Trend Is Backand More Elevated Than Ever Vogue Dress Over Jeans Y2k 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. Rachel Bilson hopes 2000s trend for jeans and dresses returns myTalk 107.1 Katie Holmes Brings Back Questionable Early 2000s Jeans and Mini Dress Trend on the Red Carpet 2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice