Popsugar Fashion Style How-To What Clothes Should I Wear in My 40s? 40 Pieces You Need in Your Wardrobe by 40 May 17, 2018 by Randy Miller View On One Page Photo 20 of 40 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 20 Tall Boots Jennifer Connelly's and Stuart Weitzman's sky-high boots ($383) prove you don't have to show a lot of skin to ooze appeal. Stuart Weitzman Sky-High Boots $383 from stuartweitzman.com Buy Now Previous Next Start Slideshow ShoppingStyle How-To