For an outfit that delivers function and dapperness, wear a white v-neck t-shirt with blue jeans. Round off this ensemble with white leather oxford shoes for an on-trend hi-low mix. In winter, when warmth is essential, it can be easy to settle for a less-than-stylish outfit in the name of convenience. But this outfit is a practical illustration that you totally can stay warm and remain stylish in winter. Certainly a smart pick if we're talking dressing ideas for gents in their fifties.