This pairing of a grey turtleneck and grey chinos is the perfect foundation for a casually stylish look. If you need to immediately amp up this ensemble with a pair of shoes, introduce a pair of black suede loafers to the mix. Seeing as temps are getting lower, this look is a good choice for the time in between seasons. This outfit shows that figuring out how to dress well at 50 and beyond is not that daunting a task.