Want to inject your menswear collection with some fashion-forward dapperness? Try teaming a black wool harrington jacket with black chinos. You can take a more casual approach with footwear and add grey suede low top sneakers to this ensemble. This one is a savvy idea if you're piecing together a standout getup for transitional weather. This combo illustrates that as an over-40 gentleman, you have a vast array of dressing options.