Do you feel confident some days and other days not so confident in your living simply

I've come across this lately and geesh I'm in my forties and should know what I want by now right?! And feel confident in my decisions! In particular, my dress and grooming. I'm pretty low maintenance....still want to look healthy and good but feel that maybe something's wrong because I don't own tons of shoes and makeup and clothes nor do I care to. Are there others out there kind of going through the same thing?

Do you feel confident some days and other days not so confident in your living simply