Wedding attire

I’m so not a bridezilla, but a bra is an absolute requirement! Perhaps you could take her shopping so she can pick out something that feels comfortable to her.

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She would wear a bra, but when my sister got married she bought thing for her to wear that covers the chest and stomach and she felt comfortable in it. This bridesmaid is a tom boy and doesn't like anything dressy or girly. She is also my sister. So yes, a bra will be a requirement, but I also know if someone doesn't like regular bras, then I will not be making them wear something and have them complain and ruin my day.

This totally depends on the dress and what you BM has going on in that department. Take her and the dress and go shopping. She may just hate underwrite, so maybe finding a wire free would work. Or she really likes the support of a sports bra, so she needs an extra supportive bra. Or if you can find a sports bra that works under the dress, maybe a different strap configuration, or what have you. But this is going to totally depend on your BM.

What is her dress like? Does she have the option to go braless, or perhaps wear a bralette of some kinds?

Depends on the dress. If it's got cups built in she doesn't need one. If it's got straps she can get those pads that just hide nipples and slip those in it. Or even just pasties honestly. Bras are fairly optional if you're smaller chested.
A camisole works, one with a little lace on top will look fine even if it peeks out a little bit.
Bralettes are really good if you don't wear a bra everyday. Some even come in the racerback style like a sport bra
Lastly my bestie is well endowed, while she doesn't have a problem with regular bras they aren't comfortable so she wears a sport bra 90% of the time, you'd be surprised how well you can get a sport bra under a dress. Slap a shrug or sweater on her if you're worried about it showing. You can find a nude one if you look hard enough.

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The whole thing is that my BM is super picky. She is my sister, so she thinks she can criticize everything. I want her to be happy, but I can not find a dress that will work with a sports bra. She only likes certain kinds. It is just so frustrating.

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I haven't chosen a dress for her yet because my wedding is still 2 years away, but I have given her options and she was like I don't like that. She would also just compare everything to our sister's wedding when she got married 10 years ago. I told her I would like a knee-length dress, but she was like well I like longer dresses because I don't like dresses at all. She doesn't like to dress up at all either, so it is very hard to work around her to make her and myself happy.

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See the thing is my BM only like sports bras and she will also not be able to go braless. She has to have a bra on at all time or she doesn't feel comfortable. She is very large chested, I wish it was that simple with her. She will need something for the dress or it will be noticeable that she is not wearing a bra; padding or not. A sweater would work... but my wedding is in August and it is on a farm and the reception is in a barn, so it will be super warm. Thank you though.

Could you find a dress with more of a back and just find a nude sport bra?

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I could. I just haven't had any luck online. I am hoping once I start checking out stores, I will be able to find something that will be perfect.

I got a lace shrug I wear on top of dresses because I just don't like being bare shoulders. It's not hot and hides bras. Maybe you look for one of those.

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Thank you. I could try that, but it isn't going to matter what I choose. She is just extremely picky and will not settle for anything because she doesn't want to wear a dress in the first place. She hates to dress up.

Pasties or a cute bralette?

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Pasties wouldn't work because she likes the comfort and support of a sports bra. A bralette would probably work, but she would never wear it again so it is a waste of money. I guess I will just have to keep looking. Thank you.

Well shell likely have some other kind of event in the future so the bralette isn't a complete waste.
I've been toying with bridesmaids in pant suits idea myself. A really nicely tailored suit looks just as good as a dress. Suits are reusable too, so that's a good investment.
There's the whole jumper fad that could work but I'm not as impressed with it. If she's a tomboy the jumper might be worse than a dress. Especially with the sport bra.

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Any other event she goes to that requires to be dressy, she usually wears dress pants and a nice shirt. But I will definitely consider the bralette.