Thanks for the comments, guys!
I'm just scared to see how different he will look but I'm sure he will still be cute as can be!
But I do think a cut like that would just be easier especially with summer nearing!! He'd probably be a lot more comfortable. Plus, we have a pool in the backyard and if he ends up liking swimming, I do not want hair like that getting chlorine wet all the time and having to brush through it!!