This ensemble with a shearling jacket and jeans isn't a hard one to pull off and is open to more creative experimentation. For something more on the elegant end to complement this outfit, complement this getup with black leather casual boots. Planning a well-coordinated combo can be a bit of a juggling act on its own. Enter extra cold temps into the equation, and the whole thing becomes even more difficult. No worries, this here is your wintry outfit inspiration. Perfect if you're in search of some incredibly inspiring style for 50-something gents.