If you're looking for an off-duty and at the same time seriously stylish ensemble, pair a charcoal puffer jacket with a grey hoodie. Go the extra mile and shake up your ensemble with grey athletic shoes. Can you see how super easy it is to look seriously stylish and stay comfy when cooler weather hits, all thanks to combos like this? This ensemble should encourage anyone who had doubts about sporting casual outfits as a 40-year-old gent.