Very amusing to me, but so sad

OK, this may sound a little paradoxical, but most people who have talked with me or followed my Blog posts have to know I (as Lou) have a very low self esteem, that's the reason I dress as Louise.

So the strange part of this little post is:

Last week I found a pair of like new women's riding boots at a Thrift Shop. They fit well although they were very stiff at the ankle area and I wanted to break them in, but I wasn't dressed as Louise. I usually wear women's jeans anyway and the boots have about a 2" stubby 1"x1" tapered heel (like the old Cuban heel style) and the style and shape are like women wear with Jodphors for horse back riding in a Tan color.

I stopped in at the local WAWA for a cup of coffee, the price was 1.07 for the last month and I go in with exact change, when I went to pay, the cashier said the special was over and it went up, I said no problem, I'll get the extra change. I went out to my car and an older gentleman (about 60's) comes up behind me and says, I'll pay for your coffee. He had to be just behind me in line and heard me say I had the money, I wonder why he offered to pay for me (maybe the boots)?

My confusion is, I realize everyone noticed the boots as I walked into WAWA, you have to walk the Gauntlet (so to speak) because the check out counter is where you walk in and every ones heads in unison (like 8 people in line) looked down at them. So was this person affected by the way I was dressed, it had to be, because he never met me before and we had no conversation. Would he have done the same thing if I was just dressed "normally", that is my question and what makes me sad.