I'm 29 and work for the Government. I wear my Nano with the LunaTik and it looks great. Keeps my music close since I don't want to kill my iPhone listening to music all day.
The LunaTik overall is probably the "classiest" of the bands that are out there but it is a little expensive.
Hex makes a few that look nice. The one with the metal band looks the best.
I have used a bunch of watch bands and the LunaTik is the one I stick with. I do also like the Griffin Slap. It was only 10 bucks on amazon and it is a slap bracelet with a ton of protection. I wear it when I skateboard on the weekends.
As for the price, $129 is nothing for an awesome watch, especially one that plays music. I have a couple of G-Shocks and each of those cost more than the Nano. Other than them being rugged, they offer less features.