Reach for a black shearling jacket and black skinny jeans for a casual and trendy outfit. Let your sartorial sensibilities truly shine by finishing off this outfit with black athletic shoes. Picking out a cool combo can be a bit of a juggling act on its own. Enter uncomfortably cold temps into the equation, and the whole thing becomes all the more difficult. No worries, this here is your winter outfit inspiration. This ensemble should erase any doubts you had about wearing casual clothes as a man in his 30s.