If you're in search of an off-duty yet sharp getup, wear a grey puffer jacket with a hoodie. Rounding off with grey athletic shoes is an effortless way to inject a playful feel into this look. Can you see how very easy it is to look sharp and stay cozy when chillier weather hits, thanks to this getup? This ensemble should clear any doubts you had about wearing casual clothes as an over-40 gent.