You are correct; I am not a fashion consultant. Even so, he needs to ditch that haircut. He looks like an aerial view of a fishing tug making headway in heavy seas.
BTW, I’m the fashionista on the right: http://www.znakovi-vremena.net/Slike/dummies.jpg#twin%20idiots%20393x228
It is difficult to comprehend the enormity of Weird Al's accomplishment since he sported his new, hip look. He is idolized by millions of young fans and is a sex symbol for millions of young women. His new album is sitting atop the Billboard charts (entered at number 1 with a bullet!) and his popularity exceeds that of every "young" star of today, including Justin Bieber, Britney Spears, Beyonce, Lady Gaga and all the other pop stars of the current era.
Weird Al is 54 years old but he might as well be 24 because he sports a youthful appearance and is extremely relevant to the 18-34 demographic. What's even more amazing is that he has decades ahead of him to take his career to even more stratospheric heights. He's been making recordings since 1979 but you get the impression he's only getting started.
Yes, "Weird Al" looks weird and closely resembles Tiny Tim - but in show business, that's not a bad thing at all. It has separated him from the crowd and given him a virtual monopoly on song parodies (most of today's biggest music stars are literally begging him to interpret one of their songs).
Think about it. Weird Al Yankovic is more popular among the young people today than Mick Jagger, Paul McCartney, Prince, Bruce Springsteen, and even Elvis Presley. This is an astonishing achievement and when all is said and done, Weird Al could well end up being the most popular and successful entertainer in the history of pop music - with respect to longevity and consistency.