Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Vintage 2000s Men's Banana Republic Distressed Boot Cut Jeans, 35 32 Ian Drummond Vintage Vintage Y2k 2000s Strapless Denim Dress with Belt Pleated Mini Jean Dress for Women from Dhgate Basic & Casual Dresses price 79.88 Lunivop Women's Blue Gothic Y2k Ripped Jeans Baggy Harajuku Denim Trou lunivop 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.