Dress Over Jeans Trend From the 2000s PS Fashion 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. 2026*19 dresses over jeans outfits + styling tips! 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.