It's especially aggravating because the game gives no real reason for why you can't obtain the items. For example, the leather hood is one of only 2 unenchanted light armor hoods in the game, yet for whatever reason you can never obtain one. You can never get the cool gear worn by executioners either.
The whole draw of the Elder Scrolls series is that you can do what you want and be whoever you want... but Bethesda has for whatever reason make some of the cooler gear unobtainable.