I don't know if this is related to transition or age, but these days I wear chinos instead of jeans and oxfords instead of motorcycle boots. It gives me a kind of 1950's look that I really dig. Also, it's SO MUCH MORE COMFORTABLE. Chinos are softer, and much lighter weight (important in a hot climate). The oxfords have squishy soles because they're aimed at people who stand on their feet at work a lot. No one in my life was surprised by this, as I've worn men's clothes since I was a teenager and didn't wear makeup back when I thought I was just a woman who desperately wanted to be male. Actually, nobody was really surprised when I came out as trans, either, come to think of it...