I'm glad that you have decided to wait before testing the idea. As has been explained here, it is full of risks, and you need to be absolutely sure that you are willing to take those risks.
Yes, it is possible that you will find yourself without a job. Some of your "friends" may shun you. You may find that those you work with will tell everybody you know. Be careful.
If you are reluctant to ask HR outright (and the HR folks are NOT your friends), you could ask about wearing a kilt. It is male clothing, but cooler than pants. The reaction will tell you lots.
Good luck, and proceed cautiously!
