Again, we are looking at perhaps the greatest recording artist of the 21st century here. "Weird Al" has another 30 to 40 years to rack up more number one recordings. Bigger than Elvis. Bigger than The Beatles. Bigger even then Aspirin Echo - who you haven't heard of yet but will be a major force in the 2030s to 2050s.
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