This combination of a black denim jacket and a black crew-neck t-shirt is the ultimate off-duty getup for any modern gentleman. Avoid looking too casual by finishing with a pair of black leather casual boots. As you can see here, this look is a really good choice, especially for in-between weather, when the mercury is starting to drop. Men wondering how to wear edgy casual dressing as you drift through your 20s, you have your answer.