This off-duty combination of an olive bomber jacket and navy sweatpants is capable of taking on different forms according to the way it's styled. Wondering how to finish off? Introduce a pair of athletic shoes to your look to mix things up. On not-so-bone-chilling afternoons, you can wear this transitional getup and look absolutely awesome. This outfit is a huge inspiration to anyone who was cautious about sporting casual outfits as a 50-year-old man.