Wow, thx for the number of posts thus far to my question! I appreciate the feedback, and support of "just be and ride happy".
I think it has struck a cord in a couple ways for me...
In terms of my life in general, being 40, I do most certainly care less about what others think (sometimes not at all, as long as it's not purposefully hurtful). I think it comes from experience in living, and knowing how you feel in your heart alone at the end of the day is what matters. To the wind with the rest.
However, with my riding, I have definately made progress, but still feel very unsure and insecure in ways. So maybe that makes me of adolescent age in that respect? I'm breaking away from mom and dad to be independent, but still need some reassurance "is this ok" sorta thing.
As mentioned, there are definately riders who have very strong opinions about fashion and gear for the road on "looks" (regardless of age). I don't really know where that comes from originally?
I think I won't worry about it, and just ride my heart out. If I get ditched by the bike fashion police, I'll have my yellow jersey puppies to keep me company.