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