This outfit with a black leather bomber jacket and a white vertical striped short sleeve shirt isn't so hard to pull together and leaves room to more sartorial experimentation. In the shoe department, go for something on the more elegant end of the spectrum by finishing off with black leather casual boots. As the weather gets warmer, it's time to shed those heavy winter clothes and opt for an ensemble that's lighter, like this one here. Those wondering how to dress stylishly as you pass the big 3-0, you have your answer.