I've pretty much had my CJ in green low tops all throughout the game until recently. I also update his chains and watch whenever I possibly can. Here is a documentation of his style-evolution:
1) Bandana on the head, tied in the front, and a bandana to cover his mouth, both to make him look like one of those crazy gangstas you see on those Bloods and Crips album covers.
Green army jacket (not camo, just a dark, faded green), grey jeans, and green low-tops. Oh yeah, can't forget the cornrows underneath that bandana.
2) I decided to punk him out this time. I gave him a pink mohawk and brown sunglasses. I made him go shirtless so he could show off his tats. I don't want to go over the various tats I got him, but the most notable one is the AK-47 going across his back. That tat just looks SOO mean when he's all buffed-out. I then gave him those black/grey camo pants, and I let him keep his green low-tops.
3) This one I made him look like a suburban drug-supplier. You know, the guy who gets the drugs from the big guys and distributes it to the dealers. I gave him blonde cornrows with a black sunhat. Throw on some black sunglasses and a skyblue shirt. Some black khakis and brown mountain boots and you're ready to go. All he needs now is a Hummer to drive around and scout out various high schools.
Heh, dress-up Barbie for guys.