This classic and casual combination of a blazer and a brown cardigan is very easy to put together without a second thought, helping you look seriously stylish and prepared for anything without spending a ton of time rummaging through your wardrobe. Brown leather casual boots will tie the whole thing together. This one is a wonderful option if you're picking out a standout getup for weird fall weather. When it comes to dressing ideas for men in their fifties, this outfit is ideal.