Popsugar Fashion Style Profile Most Stylish First Ladies These First Ladies Were So Stylish, We Were Like, "POTUS Who?" April 20, 2018 by Sarah Wasilak View On One Page Photo 1 of 10 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 1 Eleanor Roosevelt Years as First Lady: 1933-1945 Her Look: She wore the heck out of a floor-sweeping evening gown and always polished off her daytime outfits with beads, gloves, or a floral hat. Previous Next Start Slideshow Style Profile