2000s Dresses Over Jeans Erin Walsh Told Me the Denim Trend That's a "Game Changer" Who What Wear 2000s Dress To Impress Party Theme: What To Wear ASAP! The 2000s Fashion Trends That Defined the Y2K Aesthetic Who What Wear 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. Nineties Milk The dress over jeans look emerged in the early 2000s (c. 20022005), during a period defined by maximalism and experimental layering. This Instagram