Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Vintage 2000 Christian Dior by John Galliano Trompe L'oeil Denim Print Silk Bias Cut Dress Timeless Vixen 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. 2000s Denim Dress Etsy Canada Vintage Y2k 2000s Strapless Denim Dress with Belt Pleated Mini Jean Dress for Women