For a laid-back and cool getup, pair a black shearling jacket with skinny jeans — these pieces fit perfectly well together. Want to go all out with footwear? Finish with a pair of black suede chelsea boots. We know it's hard to stay on-trend in extreme weather, but this look is hard proof that it's actually possible. This pairing demonstrates that as a gentleman over 40, you have a vast array of sartorial options.