Reach for a black parka and black ripped jeans to get an off-duty and absolutely dapper outfit. With footwear, go for something on the more elegant end of the spectrum and complement your getup with a pair of tan leather casual boots. And if you're after a killer outfit that will take you from winter to spring, look no further. Gents wondering how to wear cool off-duty looks as you navigate your 20s, you have your answer.