19 Red Carpet Photos That Perfectly Display How Crazy The Early 2000s Were Wearing a Dress Over Skinny Jeans Is the Easiest Way to Jump on the Boho Trend This Summer Glamour Dress Over Jeans Trend From the 2000s PS Fashion Wearing a Dress Over Skinny Jeans Is the Easiest Way to Jump on the Boho Trend This Summer Glamour 2000sdress over Jeans TikTok 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.