Dress Over Jeans Trend From the 2000s PS Fashion 2000s Outfits RICHARD TYLER Y2K 2000s Beaded Mesh Slim Maxi Dress A Part Of The Rest Which Early 2000s Style Star Are You? The Worst Early 2000s Fashion and Outfits Celebrity Outfits From Early 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.