2000s Denim Dress Etsy Denim Milkmaid Dress (M L L) Retro and Groovy Vintage Y2k 2000s Strapless Denim Dress with Belt Pleated Mini Jean Dress for Women 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.