2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear 2000s style: how to rock the 2000s fashion trends How to Wear a Dress Over Jeans 2024 Dress Over Jeans 2000s Trend 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.