First, You should check to see if the covid restrictions allow for a makeup class to happen at a shop like Sephora or Ulta.
I live about 45min outside The City(that’s what we call SF here). I don’t think you need to worry about most people’s opinion on the crossdress or androgynous look if you don’t come off totally perfect on makeup. I blend the looks when in the City regularly. No wig, light eye makeup and a skirt and blouse… rock it girl!
So, check the weather. People don’t think about the City being cold or rainy, but it can be.
If you don’t want to tuck your package with skinny jeans, and want to hide it a bit, try a peplum top…
Letting your instructor know ahead of time would be courteous, but I wouldn’t think it required. You’ll find that we are pretty accepting of gender non conforming folks here, but a heads up is just nice.
If you are interested, check out some of the drag shows while you’re here, I had a ball last Saturday at Oasis in the City. It was a hoot…
Feel free to PM me if you want to chat more about this. Have a safe trip and make sure you get out to some fun spots while you are here.