Out in my neck of the woods, it is quite common to see women dressed in jeans, T-shirts, and tennies. In fact, I've taken to wearing women's Levi jeans and gender-ambiguous T-shirts even when presenting as male and nobody has ever called me on it or given me the tiniest stare...not even my own mother. (She doesn't know about my GID yet, although I think she suspects that *something* is up. I think she's been picking up on my chronic depression.) As for underthings, well...I made that switch 100% quite a while back. I get to dress basically 100% feminine and yet it doesn't seem to attract unwanted attention in the male gender presentation, either. I don't feel like this is a compromise of my gender identity as this is how I would likely be inclined to dress anyway when being casual/running errands. Granted, I'd love to be able to throw on a cute skirt or blouse without giving it a second thought (ah, someday...hopefully sooner rather than later), but at least I am not totally without options.
The hair is more difficult, but I work in an industry where it is not uncommon for men to have long hair. I've tied my hair back in simple bands in every color of the rainbow and nobody has ever mentioned it. If anyone ever does, I figure I'll just shrug and say I must have grabbed my wife's band by mistake in the dark when I dressed that morning.
If you can start out nice and slow, like with a pair of women's Levi's (which are styled very similar to men's Levi's but have a more feminine fit), so they can see how "not-so-embarrassing-to-us-after-all" you look, you may be able to gradually feminize your appearance and wardrobe a little bit at a time as they become accustomed to it. One day, they'll wake up and realize you've been dressing in all women's clothes for quite a while and they hadn't even noticed. On the other hand, they may end up drawing a hard line in the sand where they say "this far and no further...or else!") Then you have to make the tough decision of whether to honor that line or cross it, knowing what the consequences might be.
Of course, your circumstances and results may vary.
