If it's comfort and functionality that you're searching for in an ensemble, rock a black leather biker jacket with black sweatpants. If you want to break out of the mold a little, introduce a pair of black slip-on sneakers to this look. This outfit is a really nice idea, especially for fall, when the temps are starting to drop. Think you can't pull off edgy off-duty outfits as you head into your 50s? This combo should prove you wrong.