Welcome to the Café. I second what both Fred and OldSalt1 said.
I'm 69 and started wearing skirts and dresses in public while presenting as a man in 2015. On average, excluding my brother and his wife, I have had 1 hostile encounter per year. None of them were in any way physically threatening. It's not just that I live in that hotbed of liberal, laissez-faire thinking, Portland, Oregon; I have worn skirts and dresses in 5 states and counting. I wear them to church -- it was one of the first places I wore a dress, hose and heels -- and work. In fact, I interviewed for my current job in a skirted suit, scarf blouse and t-strap heels.
I have worked with construction workers as the owner's rep in a dress and heels, bought hardware and car parts and usually go to my sports car club events in a skirt or dress. Indeed, the club president's wife introduced me to a new, female member as someone who "everyone looks to see what he is wearing."
Definitely, the case at our Christmas Party. All eyes were on me when I entered the venue in my red, sequined evening gown. I saw one woman give me a thumbs up. The other looks I noticed were approving if not admiring. In the dinner line a woman marveled at my ability to walk down the gangplank to the floating clubhouse where the dinner/dance was held in heels.
If an old guy like me can get that kind of approval, a young guy like you will knock them dead!
Trust me, I wouldn't have gotten this kind of reception 15 or 20 years ago, but today it's a whole new world!
As OldSalt1 suggested, take enough stealth walks outside that you begin to feel comfortable and then escalate. Understand that like me, every time you're about to push another self-described boundary, you'll do it with trepidation. Yes, you read it right, like me! I fully expected to not get the job I interviewed for in a skirt. Fooled me! I did it anyway because I wanted to get past that fear. Good thing I took the chance!
Not only did I get the job, but I proved to myself, once again, that almost without exception, things work better when you are your genuine self. Even when they don't turn out the way I want; I later realize, I dodged a bullet I didn't see at the time.
So, for your own sake, BE. YOUR. GENUINE. SELF. You'll be so much happier for it, you won't believe it.
And, you will inspire so many more people than you will ever know to be their genuine self.
David, the PDX Fashion Pioneer
Social norms aren't changed by Congress or Parliament; they're changed by a sufficient number of people ignoring the existing ones and publicly practicing new ones.