Pair a black overcoat with a black crew-neck sweater if you're going for a proper, sharp outfit. For times when this outfit is too much, tone it down by slipping into a pair of white leather low top sneakers. With the departure of snow comes warmer, sunnier weather and the need for a kick-ass look just like this one. This outfit demonstrates that staying fashionable as a 40-something gentleman is easier than one might think.