If you want to wear bootcut jeans, the 'toothpick rule' hack is the way to do it right 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. 2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice In the early 2000's Apparently, I loved to wear dresses w jeans @ Los Angeles, California Jessica Alba Just Reminded Us About This Inescapable Denim Trend From the 2000s