A crew-neck t-shirt and black chinos are a pairing that every dapper gentleman should have in his casual collection. Complement this ensemble with yellow leather high top sneakers to immediately boost the cool of your ensemble. In the winter months, when comfort is crucial, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is a shining example that you can actually stay comfortable and remain equally stylish during the winter months. Laid-back outfits for stylish middle-aged guys aren't actually that hard, as you see here.