This pairing of a shirt jacket and black and white dress pants is a never-failing option when you need to look truly smart. Let your styling savvy really shine by finishing this ensemble with a pair of dark brown leather chelsea boots. When leaves are falling down and autumn is setting in, you'll love this outfit as your favorite for transeasonal weather. As a 30-something gent, you want to start dressing in a more sophisticated manner. That's when outfits like this are a safe option.