This relaxed pairing of an overcoat and blue ripped jeans is a real lifesaver when you need to look cool in a flash. To bring a bit of classiness to your look, introduce a pair of derby shoes to the equation. When it comes to dressing for fall, nothing beats a cool combo that transitions easily between seasons. Think you can't pull off edgy off-duty looks as you head into your 50s? This pairing is indisputable proof of otherwise.