^^My two cents on the haircut, because these are the things that interest me...I've seen a lot of people doing their hair like that in Chicago, and I imagine it's big in the rest of the world...that being said there are only so many hairstyles to work with, so if you like it go for it...just don't, like, completely shave the sides.
I had a similar hairstyle back in 2011 after a crappy break up
and it was nice to have a different hairstyle than the mop top I just usually rock...but I had to stop doing my hair up when my mother, of all people, pointed out to me that I have a large forehead(what some would call a "fivehead"). I inherited it from her...
The only other real problems I had with doing my hair up is that you'd have to find a hair product that you're comfortable with(I spent so much on hair products that I used once or twice) and it tends to require frequent trips to the salon to look nice and tidy.