I want Silas Botwin's hair

I'm hoping someone can give me some hair styling advice. I've had a short military-like and/or spikey haircut all my life and I like the way I look, but I'd like to at least give myself a shot at a different style. I LOVE the way Silas Botwin (Hunter Parrish) from Weeds had his hair (pic below) and there's some other men's styles too that are similar, but I don't know how to go about getting my hair like that. Do I let it continue to grow and then go to a salon or should I go to a salon now and get it styled as time progresses? Also, what do I ask for when I go to a salon? Do I just show them a photo of what I want? Do I HAVE to go to a salon or can a barber do the same thing?  Please, I'm totally clueless. Thank you in advance.

That's me in the mirror pics below. Not that it matters or maybe it does, but I'm a big, stocky, 6'4" linebacker type guy. Do you think it will look good or am I going to look like an idiot? I'm 39 years old.

Thanks,
Beau