2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice Vintage 2000s Y2K Cop Copine Subversive Prairie Milkmaid Style V Neck Thee Cultivator The Worst Early 2000s Fashion and Outfits Celebrity Outfits From Early 2000s Vintage 2000s Y2K Cop Copine Subversive Prairie Milkmaid Style V Neck Thee Cultivator 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.