This combination of a grey herringbone overcoat and a black turtleneck looks polished, but in a cool kind of way. To infuse a sense of stylish casualness into your ensemble, introduce a pair of black leather low top sneakers to this ensemble. Seeing as temps are dropping, this outfit appears a good idea for the transitional season. Gents who are curious how to pull off edgy casual dressing in your twenties, you have your answer.