Hey,
From what you've said you want, if you want a suggestion... we should build upon your pic 1 and 4.
Hair, go with the slick back look. It will give you that manly look you want, and you have thin hair, slick back will work (can't really tell if thats what you have on pic 1 and 4)
Clothes. You need better fitting clothes (not so tight that it makes you look like Jersey Shore douchebags). I don't mean any disrepect, but you gotta admit the clothes on pic 2, and 3 are not that flattering. The reason for them not being flattering is because they don't fit you properly and the fabric of the colors are not bright enough (that doesn't mean you need to go wear bright yellow or red; a good quality clothes will give you a brighter color even if its green or beige). You want to focus more on well fitted shirts (don't get t-shirts, those are for high schoolers; if you much, a solid color v-neck would suffice). Flip through GQ magazine or go to Askmen online magazine. They will give you much detail about how to work different shades of denim jeans or how to work the gingham shirts. And please, no sandals with jeans, I might just have to call the fashion police on you

If you don't feel like wearing socks and too lazy to tie shoelaces, go to Aldo and pick out some loafers. They're like only $90, its slip-on, no socks required- convenient, cheap and fashionable.
You might want to get some leather jacket to go with your look too.
Let me know if you have any other questions! happy to help a fellow friend.