I chose a high-end LBS despite feeling intimidated, then crashed one of their bikes on my first test ride.
I was off my bike for seven months after the crash. First because of injuries, but later because of fear.
I still have to overcome a little sliver of fear before I start every ride.
I ride with a mirror and a front flasher. I remove them whenever I'm stopping by my high-end LBS.
I have SPD pedals on my road bike and my shoes are so old/cheap that they lace up. No velcro, no clasps.
I don't own a real cycling jersey (though I have finally ordered one).
I have only one pair of bibs and they have to line-dry, so I only wash them every fourth ride or so.
I tell myself I don't care if other roadies think I'm a Fred. (I'm lying.)
I live in the mountains, but I don't like hills. I gravitate toward the flatter routes I can find.