After trying several failed styles I swallowed my pride and went to an eyewear boutique... Not like Sunglass Hut but a really upscale place in the fashion district. I'm not at all metro but I figured the premium price would be worth it to get a hot babe to tell me what looked perfect on me.
Ended up with the Mosley Tribes "Colden" aviators in my avatar (~$200). The attendent explained how with bald guys, the big tear-drop frames offset the size of the forehead and compliment the curve of the skull. Who knew. Might explain why many rappers wear the larger frame shades since most of them have shaved heads.
Anyway if you go that route, dress as you would for a date so they'll pick a style of frame that matches your style of dress.