He gots that swag, baby...check out his custom 1989 Oldsmobile Cutlass Ciara--with Louis Vuitton paint job. If this was a blind date and I saw this car, I would not even open the door. I would hide. Permanently.
Wear something that makes you feel good and that you are comfortable in. Accessories like hats are great for creating different looks without actually changing your entire outfit and are wonderful tools for adding a splash of colour to the images.