Hey, you do what works for you! There's no "right" way of doing any of this. You love riding your bike and you're going some nice long distances, so who cares what you're wearing or how you're learning? Besides, given the story you told about learning to ride as a kid, it seems like you learn best when you're teaching yourself and learning through trial and error (although I don't recommend throwing down the bike this time around).

In 1990 on a complete whim I decided to take a year and cycle around Europe. I hadn't been on a bike since probably 1985 or so and I knew precisely nothing about touring (and didn't even have the internet to teach me anything quickly). So I went to a bike shop, lucked out and got a good touring bike, stuffed my panniers with shorts and freebie cotton t-shirts and cheap socks from K-Mart and I left. I wore those clothes most of the year (switching to jeans and a sweatshirt when the weather got cold). I cycled in whatever kind of shoes I had (I think it was a pair of Tretorn sneakers and some LL Bean boat shoes). I had one water bottle. I couldn't afford better and even if I could have I wouldn't have known that better was available. I probably covered 8,000 miles dressed like that and lived to tell the tale (and what's more, when people ask to hear the tale they never ask what I was wearing). I laugh at myself now--I can't go to the gym and run on the treadmill without carrying a bag that's bigger than what I had for that whole year and wearing clothes that are so technical that they interrupt electronic signals. OK, I'm exaggerating. But I'm not having any more fun now than I did back in 1990, and I'm certainly not any faster or stronger. The only regret I have is that now that I can afford good cycling clothes I no longer look good in them. I would have looked awesome in spandex when I was 21. Aging sucks.

Sarah