For a look that's street-style-worthy and effortlessly smart, marry a beige puffer jacket with chinos. White and black leather high top sneakers will bring a dose of stylish effortlessness to an otherwise standard getup. This getup is a viable pick if you're on the hunt for a killer outfit that transitions easily into fall. When it comes to casual fashion tips for gentlemen in their 50s, this outfit looks great on most.