Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium 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. 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 Dress Over Jeans Trend From the 2000s PS Fashion