Extra stylish, this relaxed pairing of a bomber jacket and a long sleeve shirt provides with wonderful styling possibilities. For something more on the classier end to complete your look, introduce a pair of black leather chelsea boots to the mix. As you can see here, this getup is a really wonderful pick, especially for transeasonal weather, when the mercury is dropping. This outfit shows that figuring out how to dress well at 60 and beyond is not particularly hard.