Try teaming a black hoodie with black ripped skinny jeans if you seek to look casually dapper without spending too much time. Puzzled as to how to finish your look? Wear a pair of plimsolls to polish it up. There's no better way to cheer up a bleak fall afternoon than an on-trend outfit like this one. Now that's an ensemble that's guaranteed to make you stand out among other 30-something Millennial chaps.