Katie Holmes goes full Y2K with Jingle Ball 2022 outfit 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 If you want to wear bootcut jeans, the 'toothpick rule' hack is the way to do it right