And heres me wearing a wig from an old halloween costume. If my hairs similar to this itd be tough not to grow it out. 

Yeah dude, you should really try it, honestly. I'm guessing you're in your late 20's, and at this point you will probably have to consider that you won't have the same coverage for a lot of longer. You don't have much to worry about with your looks when that happens, but the next few years are probably your last chance.

The wig length really isn't out of the question if you start now, especially considering the texture you get out of your hair in the car part of the gif. And to be honest, it does look really great on you. I'd really suggest going for it. There's a few subreddits around if you need encouragement through the awkward stages. The short on the sides look is alright, but it seems unfortunate to stick with that if you want to try longer, and you've gotten this far.