In the early 2000's Apparently, I loved to wear dresses w jeans @ Los Angeles, California Jeans Under Dress 2000s 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. Are You Ready for Dresses Over Jeans Again? The New York Times 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.