A turtleneck and white jeans? It's easily a wearable look that you could rock on a daily basis. To add a little fanciness to your outfit, introduce dress boots to your outfit. Figuring out a cool ensemble can be a bit of a conundrum on its own. Add extra cold temperatures into the equation, and the whole thing becomes all the more difficult. Fear not, this here is your winter inspo. Combinations like this have a sophisticated air that befit guys in their 50s really well.