Vintage 2000s Y2K Strapless Denim Dress Second Shift Vintage Chicago, IL ATTIC 2000s Denim Dress 2000s Denim Dress Etsy 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. Denim Milkmaid Dress (M L L) Retro and Groovy 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.