man....i totally feel what you're saying...I am not wearing yet as I am still struggle with the thinning hair and concelears and in the last years I felt the same as you. "I've always had that feeling of inadequacy since I was so young when it started."
sometimes I am telling myself..."fuck it I will shave my head, then when I am looking in the mirror with the hair concealed...I am saying myself that I need to do something regarding the hairloss and will never show the bald scalp...it is a fight inside of me that puts me often in depression.I have lot of friends ...95% of them have great hair...and I feel horrible about myself especially when they are joking about bald people.
I guess that once you will get used with the routine and the piece will look more natural you will gain more and more confidence...I mean...there are lot of guys that are wearing and feel great and look great...not all of them look great tough...just think that there's no other viable solution out there....can u post a picture of you to see your style and look?