This combination of a navy v-neck sweater and jeans makes for the ultimate casual style for any modern guy. If you need to immediately up the style ante of your outfit with a pair of shoes, why not add a pair of dark brown leather brogue boots to this ensemble? Rest assured, this combo will keep you cozy as well as looking seriously stylish in this in-between weather. This pairing shows that figuring out fashion over 50 is not particularly hard.