One of the coolest ways for a man to style out a windbreaker is to pair it with black jeans for an off-duty ensemble. Introduce a pair of black casual boots to your ensemble for an added touch of style. So if you're on the lookout for an ensemble that's sharp but also entirely spring-appropriate, this one fits the task well. Ideal if you're looking for some incredibly inspiring casual style for 30-something Millennial men.