Dress Over Pants: Is There A Stylish Way Of Wearing It Sans The Y2K Nostalgia? Elle Fanning Resurrected The Dress Over Pants Trend From The 2000s 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. How Street Style Stars Do the Dresses Over Pants Trend