You are confusing spiritual freedom with wanton disregard of work place rules and ethics, and in some respect, criminal offenses. What this guy is doing to you has nothing to do with his "style" or "free spirit", which I can only understand as excuses you have come up with for him out of your good hearted attempt for empathy. You are rationalizing your unwillingness to report him the HR or other authorities. By doing so, you are essentially tolerating and even encouraging him to further his offensive behaviors. You are doing a disservice to yourself and to all other women. The so called "free spirit", or this particular manifestation of freedom to harass women, needs to be stopped. i am not sure why you are so convinced that HR would not be able to impact his behavior. If he is indeed that type of person, then a call to the police seems to be in order. Law enforcement does not always stop bad guys, but that is certainly not the reason not to report crimes so there is at least a chance to catch criminals and change their behavior in the future. "Pit" or not, I find your making the "free spirit" excuse for him just as disturbing as the harassment itself.
This morning, I joked around with you. This time, I am being serious. Now I have covered all my bases.
Happy Holidays!