Dresses Over Jeans: A Retrospective : r Fauxmoi Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Vintage Y2k 2000s Strapless Denim Dress with Belt Pleated Mini Jean Dress for Women from Dhgate Basic & Casual Dresses price 79.88 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.