Go for a charcoal herringbone overcoat and blue jeans, if you prefer to dress for comfort but would also like to look dapper. You can get a little creative when it comes to footwear and complement your look with white and blue leather low top sneakers. As the weather starts to improve, it's time to get rid of those bulky winter gear and opt for a look that's lighter, like this one here. Those who are dubious whether you can still wear cool casual looks as you head into your 50s, you have your answer.