The first look is obviously quite different from the second. The first is short on the sides (and back) with much longer lengths on the top (probably different lengths) and would really just require some gel, and if you want it to stay in that shape throughout the day, some firm hair spray (maybe some blow drying?). It's high maintenance (sp) (IMO).
The second is really just a short haircut, color, and gel, strong pomade, and sunglasses.
IMO, high maintenance is out.