If it's comfort and functionality that you're looking for in menswear, consider wearing a black leather biker jacket and grey chinos. Finish your getup with a pair of black leather loafers to serve a little outfit-mixing magic. As you imagine, this is a cool choice come warmer weather. As a guy in his 30s, you want to start dressing like a grown-up. In this case, looks like this are ideal as inspiration.