2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice 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. Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium The 2000s Fashion Trends That Defined the Y2K Aesthetic Who What Wear