Head wraps or wigs

[Amari]

So I have not yet begun my transformation  with hRT however I often times dress like a female, and feel as though I most closely mimic a female when I have a head wrap on verses wearing wigs. I have tried lace fronts, full lace , human hair and synthetic, I have had weave, and extensions. But I feel most comfortable with the head wraps. My boyfriend however feels that I look passable both ways but prefers the wigs. I know that eventually I will have no choice but to wear wigs or my natural hair out but the head wraps are my security blanket.  As I stated I don't feel passable with wigs. Any advice guys , do I appear passable with the head wraps?  Should I switch between the two ? My boyfriend insist that I become more confident and says the head wraps prevent me fro doing so, I agree to a certain extent