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 Denim Dress Strapless Mini Dress with Belt The Feelz Y2K Denim Mini Dress: Sleeveless A Line, Backless Ruffle Frock Vintage 2000s Korean Fashion Summer Party Dress Buy Now! Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life Vintage 2000s Y2K Strapless Denim Dress Second Shift Vintage Chicago, IL ATTIC 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.