Popsugar Fashion Michelle Obama First Lady Fashion All Hail! These Are the Best First Lady Fashion Moments of All Time July 22, 2019 by Rachel Aschenbrand-Robinson View On One Page Photo 2 of 22 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 2 Jacqueline Kennedy The new First Lady was impossibly chic in a simple sheath for a portrait with Caroline in 1961. Previous Next Start Slideshow Michelle ObamaNostalgiaDressesFirst LadyJackie KennedyFlotus