Dress Over Jeans Trend From the 2000s PS Fashion 6 ways to style dress over jeans as the controversial Y2K trend makes a comeback for autumn Are You Ready for Dresses Over Jeans Again? The New York Times Try Not To Cringe At These Early 2000s Fashion Trends Local Bahrain 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.