This outfit with a navy plaid wool blazer and a white dress shirt isn't a hard one to pull together and easy to change. Why not complement your outfit with navy suede espadrilles for an element of stylish nonchalance? When it comes to dressing for transitional weather, nothing beats a killer look that will keep you comfortable and looking your best. Wondering how to dress as you go into your 50s? This combination is the perfect answer.