Hi NJD, and welcome to the forum! I'm also in my mid-fifties and love the boots and tights look with dresses. I like to shop for dresses at Macy's, Nordstrom's, Ann Taylor and Talbots. Now that the weather is turning cooler, keep an eye on the forum and you'll see lots of members posting pictures with boots and dresses. Frye boots are a big favorite here.