Thanks for all the input everyone! I don't mind honest feedback, good or bad, to help me learn my way around this.
I will increase aperture when I go take more shots today. I did notice the shirt being crooked and his hair being all over the place - I was trying to snap these pictures while he was on the move on a windy day, so I couldn't do too much about that
About the lighting - does it look flat? In trying to keep the post processing to a minimum, did I leave his skin tone too cool or not increase the contrast enough?
Also, I'm not sure what caused the hair on top of his head to look like that, I tried to keep the PP to a minimum, but like I said, yesterday was my first try so I still have a LOT to learn.
Thanks again for all the help, it's appreciated!