Popsugar Fashion Celebrity Fashion First Lady Fashion All Hail! These are The Best First Lady Fashion Moments of All Time 21 June 2018 by Rachel Aschenbrand-Robinson View On One Page Photo 2 of 21 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 Celebrity FashionFirst LadyJackie KennedyFlotusNostalgiaDressesMichelle Obama