2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice Dress Over Jeans Trend From the 2000s PS Fashion A Dress Over Jeans: Fashion Disaster or Statement? The Bruinista 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.