I had doubts for years, I'm 71 and have been dressing for well over 60 years. But somewhere at around 30 or so, I realized this is who I am, I can't survive with out dressing, not and find any happiness in life. I stopped many times in my youth, it always left me depressed, resentful, angry, and argumentative. I didn't even like myself, and I don't see how others put up with me.
Then I remembered something we used to say a lot in the sixty's, " If it feels good, do It", well it does feel good, so I quit worrying about it, and I just do it.
For the last 30+ years, life has been good, I dress when I want, and I never have doubts about it, except, how an outfit looks, or did I get my make up right.