Popsugar Fashion Red Carpet Best Emmys Dresses Ever 55 Absolutely Breathtaking Emmys Gowns That Deserve Their Own Award September 21, 2019 by Randy Miller View On One Page Photo 42 of 55 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 42 Calista Flockhart in 1999 No dress, no problem for Calista Flockhart, who wore an of-the-moment shirt and skirt combo in 1999. Previous Next Start Slideshow Red CarpetEmmy AwardsAward SeasonDresses