For relaxed dressing with a modernized spin, you can easily dress in a grey crew-neck sweater and navy jeans. To give your overall ensemble a more relaxed touch, why not add white and navy leather high top sneakers to the equation? In the winter months, when warmth is imperative, it can be easy to surrender to a less-than-stylish ensemble. But this ensemble is a clear example that you totally can stay comfortable and remain equally stylish during the winter months. A practical example for anyone who's still figuring out how to dress as an over-40 gentleman.