It sounds like you got your money back on the second pair of Herman's boots, so you were fortunate on that deal. Quality boots are certainly the way to go. You will get the benefit of this additional quality every time you wear the boots, plus the boots will last longer. Be aware that if your body core or your head are dissipating too much heat -- meaning you are not wearing enough clothing/hat for the weather -- the first place you will feel cold is in the extremities such as your toes or fingers. Thus, if your toes are cold or your fingers are cold, the place to solve your problem may be put a hat on your head or pull on your parka.

If you can't just go out and write a check for all the hunting gear you want to pick up, you might consider some alternate outlets for purchases. For example, you may be able to find good deals on Pendleton wool shirts on ebay. These shirts will cost about $90 new through standard retailers; through ebay you may be able to buy for much less, depending on the specific auction. You can sometimes find good M51 Army Surplus wool pants in the appropriate size, these are excellent hunting pants. You may be able to find wool shirts at Salvation Army or Goodwill stores. Just some thoughts.