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 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. 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear Embrace Y2K Fashion: Mini Dress Over Jeans Style