A v-neck t-shirt and jeans paired together are a match made in heaven for gents who prefer casually cool looks. For something more on the relaxed side to complement this look, add a pair of light blue athletic shoes to this outfit. Needless to say, it's easier to work through an extremely hot afternoon in a cool combination like this. This outfit should clear any doubts you had about dressing casually as an over-50 gent.