This combo of a black crew-neck t-shirt and charcoal jeans is hard proof that a safe casual ensemble doesn't have to be boring. Black leather casual boots will breathe an added dose of elegance into an otherwise utilitarian getup. During the winter months, when warmth is crucial, it can be easy to settle for a less-than-stylish look. This look, however, is a vivid example that you can actually stay comfortable and remain stylish in the winter months. Laid-back looks for guys in their 30s aren't actually that hard, as you can see.