Help convincing my mom to let me dress like a boy

Tell her that you can still be the maid* of honor and wear the same kind of outfit as your brothers. *Or whatever the male version of 'maid' is.

I mean, somebody's wedding is supposed to be the happiest day of their life. Maybe not now, but looking back, would she be happy seeing her son in a dress in the pictures knowing it made him [you] unhappy and she was the one who forced him to.

You could always bring a spare male outfit and change when some people start arriving. She wouldn't want to make a big scene on her day, so she'd let it slide [hopefully].

Ask her that, if you were a cisgirl, would she make you wear the dress even though she knew it would make you unhappy? If the answer is no, then the answer should still be no knowing you are a transboy and wearing a dress would make you unhappy. [Not sure what to do if the answer is yes though]

If any of that doesn't work, you could try finding a more masculine style dress if they make those.

 

I would be like "sorry, can't be your maid of honor, I'm a dude remember?" Fortunately you have a long time to come up with a solution.

 

I had this issue with my sister... She was absolutely positive that I would be wearing a frilly, long dress (to match all the bridesmaids) and because she wouldn't listen to me telling her that I would rather be completely naked, I told her I wouldn't go. She had a very, very big tantrum, but eventually said that I could wear what I wanted as long as I didn't expect to walk down the isle with "the other bridesmaids", which I was fine with because I didn't want to be a bridesmaid anyway.

I don't know what your relationship with your mother is, but it may be a viable option to simply say "I wear something else or I don't go". If you put it into perspective by saying you expect to be further along in your transition by then, she might realise just how awkward and uncomfortable it'd be for you and also her. Having her son standing awkwardly in a dress off in the corner isn't an ideal memory for her wedding day.

 

Try to remember that it's your moms big day, planning your wedding is almost as self-centered a process as transition. So, it's no wonder she won't listen to you any more than you would listen to her about your transition. That said, I don't think you should do something you're uncomfortable with. Put your foot down, you go as you or you don't go. But you can't make that threat and then give in, you have to be a man and stick to your guns even if you miss your moms wedding or she will always push you and think she can call your bluff.

Before I get into my story, let me point out that I'm not saying you should handle your mom like I have to handle mine. My mom is very emotionally abusive, my case is extreme. But the point of my story is that you have to decide how much you can involve an unaccepting parent in your life while still being fair to yourself. You deserve to be accepted and don't have to settle for less.

Not to sound cold, but the threat of being cut off by your kid will make most parents get over alot. My situation with my mom is complicated: she's nuts. like 700 club + creationist-homeschooler nuts, and childhood was a nightmare as a trans kid. The entirety of my 20s was spent undoing the mess she made. Just being in her presence fills me with negative emotions, she brings out all the old negative feelings I've tried so hard to leave behind. So I have been thinking about cutting her off entirely since I was a teenager. Anyway. Throughout my adulthood Ive made a point to distance myself whenever my mom would try to interfere with my life. She's the polar opposite of me and sided with my ex wife durring the divorce. I have maintained contact with my mom mostly for my daughter's sake, and she has done a pretty good job of keeping her opinions to herself. She has even been friendly towards my partner. But, the rules are clear: mom plays nice or she's out of my life. It's harsh but given the circumstances it's the only way I can keep her in my life at all.

 

First of all, I'm SO sorry that you're having all this stress. I am by no means an expert at giving advice, but I would say to give it time. You have several months to convince your mum. I would also suggest asking her to have a sit-down discussion about why you would not feel comfortable wearing a dress. With any luck, she'll understand a little bit more, and hopefully be more open to you dressing in a way that you are comfortable.
I really hope that you come to an agreement that makes everyone happy. Good luck!