I Never Thought I'd Wear a Dress Over JeansUntil I Found This Perfect Combination Glamour How to wear dresses over pants, according to fashion creatives Vintage Y2k 2000s Strapless Denim Dress with Belt Pleated Mini Jean Dress for Women from Dhgate Basic & Casual Dresses price 79.88 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.