The Y2K Dress Over Pants Trend Is Backand More Elevated Than Ever Vogue The Worst Early 2000s Fashion and Outfits Celebrity Outfits From Early 2000s Dress Over Jeans: Love It or Hate It? 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.