This pairing of a waistcoat and navy jeans is a safe bet when you need to look like a maverick in the menswear department. A pair of brown desert boots immediately ups the street cred of your look. In winter, when warmth is imperative, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. However, this ensemble is a bright example that you totally can stay toasty and remain equally stylish in winter. As an older gent, you're guaranteed to like this combo.