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 from Dhgate Basic & Casual Dresses price 79.88 Naomi Campbell Ends Paris Couture Week in an Upside Down $65,000 Balenciaga Dress Marie Claire 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. Dresses with Jeans: A Controversial Fashion Trend from the 2000s