IMO, go for quality and fitment.
After seeing your pic, Josh, I know you are pretty thin. You should stray away from a traditional fit as they look like parachute on thin guys. Go for a "slim" "stretch" or "fitted" cut. I think a GREAT site to start, just even to learn is:
http://www.brooksbrothers.com/IWCatS...Section_Id=205
Start to note the collar design, collar cut (in front), button placement, cuff design, pocket or no, etc etc.
I prefer a simple slim shirt, standard collar and button cuffs for most suit wearing. If I'm feeling "Wall Street'ish", I will go with the white collar, blue striped shirt, and big cuff links. If you are wearing them alone (no jacket), ones without front pockets look much cleaner.
Going back to quality, I have found Brooks Brothers to be of outstanding quality. I have three from Kohl's as well that aren't too bad, but certainly won't last. Express makes very nice shirts, too, a bit more trendy. I also have a bunch of Banana's, Diesel, and a couple various brands.
I have about 25-30 collared shirts in my closet now (was big into them in college).
Hope this helps.