Time to update my style (input appreciated)

That style is probably going to be a bit hard to get...your photo is dark, but it looks like your hair is curly, right?  If I'm wrong and its not curly, you are good to go, just get the tips highlighted, get it cut shorter and use gel to muss it up and make it stick up and to the side like that. 

If your hair is curly, that's going to be a lot of upkeep.  You will either have to straighten it yourself with a straightening iron (which will take a long time and need to be done every time after you wash, and may not even be possible on hair as short as his), or, you will have to grow it longer (like it is now maybe enough, not sure, you'd have to ask at the salon) then have it chemically straightened, then cut, highlighted, and styled like I said above.  That can also be a pain because when the roots grow out it will be curlier on the roots and have to be redone frequently. 

If your hair is curly and you don't want to go through that effort, forget the Brad Pitt style and you can cut it much shorter, or grow it long, either would look good on you.