This classic and casual combination of a navy puffer jacket and navy jeans is very easy to pull together without a second thought, helping you look amazing and prepared for anything without spending a ton of time going through your wardrobe. When it comes to shoes, go for something on the casual end of the spectrum by sporting a pair of black canvas high top sneakers. Relaxed combos for stylish 40-year-old gentlemen aren't actually that hard, as you see.