OK. First of all your biggest worry should not be from wearing clothing of the another gender. It should be from wearing it badly. Most crossdressers or beginning TG g-male have terrible taste in fashion. A lot of genetic women have bad taste, too, but this is more important for genetic males for obvious reasons. No matter what your body shape for facial features there are clothing, hair and makeup styles that can look good on you. Try to avoid cliche crossdresser fashions like fishnets or animal prints. If you look good people are much more likely to accept you. This will be true whether you are on HRT or not. Get some fashion education and find out what works best with your looks. And keep your femininity understated, at least at first.
There's no rule that you have to dress completely as a man or as a woman all the time. These days many males and females wear practically the same thing, anyway. Start buying your t-shirts and jeans in the misses department. You could completely replace your "men's" wardrobe before anybody really takes notice. Once you're wearing women's wear all the time already, expanding to girly things like heels or skirts will be easier for you.
