Such staples as a windbreaker and a crew-neck t-shirt are the perfect way to inject played down dapperness into your day-to-day off-duty routine. When in doubt as to the footwear, add white leather low top sneakers. Can you see how very easy it is to look dapper and stay cozy come cooler days, thanks to this look? And if we're talking casual style for 50-year-old gents, this ensemble looks good on almost any guy.