Consider pairing a black and white varsity jacket with a black crew-neck t-shirt if you're after an outfit option for when you want to look laid-back and cool. If you want to effortlessly dress down your outfit with one item, introduce a pair of black athletic shoes to the equation. As days are getting cooler, you'll discover that an outfit like this is ideal for autumn. And if we're talking casual clothing for over-50 guys, this look is perfect.