I have ventured out hundreds of times without any issues. I can't think of any challenges I have not met. No problems. Zero. The most frightening was being introduced as Susan to someone I work with. She later grabbed me in a drunken embrace. No recognition. If you can survive that you can survive anything. Some shop assistants have even assumed I am a woman which amazed me as I do not think I pass. I have had numerous compliments on my poise, my legs and my figure. It has ALL been good. Nothing negative. Now I can't think of excuses not to go out except for the hassle of completing the change in a lay-by.
Anyone who is scared need not be. Yes, you will be recognised as a cross-dresser. No, the sky doesn't fall in. No one cares if you are a man dressed as a woman, least of all shop assistants. There is something magical about that first few moments as you leave the car, putting your handbag over your shoulder, locking the car door and clicking along the road in your heels. No feeling like it. Go for it. You will love it.