How Celebrities Wore The Low Rise Jeans Trend In The Early 2000s 6 ways to style dress over jeans as the controversial Y2K trend makes a comeback for autumn It's the #early2000s & you're wearing Jeans under Dresses! #millennials #nostalgia #2000sfashion 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.