A turtleneck and navy chinos are a combo that every trendsetting man should have in his casual repertoire. For times when this look is just too much, dial it down by sporting a pair of black work boots. This one is a savvy choice if you're figuring out a standout outfit for in-between weather. This outfit is a great inspo to anyone who wasn't sure about sporting casual outfits as a gent in his 50s.