A charcoal crew-neck sweater and khaki print chinos are worth adding to your list of must-have casual styles. When in doubt as to the footwear, complete your ensemble with a pair of white canvas low top sneakers. While it can be tricky to stay fashionable in below-freezing temperatures, it's outfits like this that prove it's actually possible. This ensemble is a vivid example 50-year-old guys can still very well slay in the style department.