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. Vintage Y2k 2000s Strapless Denim Dress with Belt Pleated Mini Jean Dress for Women Dress Over Jeans Trend From the 2000s PS Fashion Vintage 2000's Denim Halter Dress by Guess Small Etsy Denim Milkmaid Dress (M L L) Retro and Groovy