This pairing of a windbreaker and a crew-neck t-shirt is pulled together and yet it's relaxed and ready for anything. If you want to immediately play down this outfit with one piece, why not add brown athletic shoes to this getup? So if you're looking for a kick-ass winter-to-spring outfit, this one fits the bill. Think it's hard for men over 40 to perfect modern off-duty looks? This combo will prove you wrong.