If it's comfort and functionality that you love in a look, try teaming a parka with a white crew-neck t-shirt. Our favorite of a variety of ways to complete this outfit is with a pair of black leather high top sneakers. With an ensemble like this in your winter collection, you'll manage to keep warm and look stylish despite the extra cold temps. And if we're talking casual dressing ideas for 40-something gentlemen, this outfit looks good on most men.