Go for a pared down yet casually cool look by pairing a navy v-neck sweater and a light blue long sleeve shirt. And if you need to effortlessly class up your look with a pair of shoes, why not introduce a pair of brown suede chelsea boots to the equation? When temps are dropping and autumn is setting in, you'll love this getup as your favorite for transeasonal weather. This combo proves that figuring out how to dress stylishly at 50 and beyond is easier than one might think.