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Erin
I would suggest you don't do anything until after the holidays. A few weeks will not make a lot of difference to you.
The pressure would be on your mom to try and understand you.
Which while coping with the holidays which can be a stressful enough time wont be easy.
Erin....my thoughts about your mom are related to my own. I was found out as well, and everyone in the family knew that I liked to dress in heels and dresses. Over the years, I kept it hidden as always, and grew up and moved out, taking my clothes with me. I do have a wife that knows about Maria and has no issue with my collection of things, and I honestly never said anything about my dressing to my first stepmother, especially since I was wearing her things when I was young. I actually told her about 5 years ago, that as you know, I like to dress and wear heels and yes, my wife knows, but I try to keep it from my boys. I know that it is tough and I just wanted to tell her, and once I did, things continued on as if I had not said anything, but I did feel much better.
Thank you for the responses everyone. Apologies for not being able to respond more thoroughly but y'know, work and all. Waiting until after the holidays may be a good call. I think I'll just play it by ear from here on out. I won't plan anything out too extensively because that'll just make me nervous, but if there's a quiet moment when we're just like, watching TV or something, I might bring it up :)