15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear Dress Over Jeans Trend From the 2000s PS Fashion 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. Are You Ready for Dresses Over Jeans Again? The New York Times Dress Over Jeans Trend From the 2000s PS Fashion Mariah Carey claims the 2000s low rise jeans trend was her idea