In the last three years, I've flown dressed and with male id from Sacramento, JFK, Dulles, Phoenix, Denver, Las Vegas and San Francisco with no problems whatsoever.
I typically wear a cotton blouse and casual knee length skirt and shoes for the season (boots or sandals).
Since then I've gone full time and I've legally changed my name. The CA-DMV lets you change the gender with a form signed by a doctor and I did a round trip from Sacramento to Cleveland. I'll admit that was less stressful and dare I say it felt normal?
I'll never forget the lady TSA agent in Phoenix, she first thanked me for having an organ donor sticker on my (then male) drivers license, then complimented me on my blouse. She seemed sincere to me!
I do sometimes worry about being seated next to someone who stereotypically I should be afraid of. On one flight, I did sit next to a big, hairy football player type. He turned out to be a great conversationalist and the flight passed in no time.
One thing to watch for is avoiding shoes with ankle straps while traveling as they can be really difficult (at least for me) to gracefully remove and put on before and after the checkpoint.
