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Fair observation. (Although I didn't say it quite as bluntly as you perhaps think.) Another indication that I need to be clear and explicit about my reason for asking.
I was just going by what you wrote:
For example, I once asked a model, through a text, "Are you planning on wearing a bra with that dress?", as the picture of the dress that she had sent me showed her wearing it with no bra. That sentence was the extent of my broaching of the subject. This appeared to make her freak out, and she then proceeded to cancel the morning of the shoot. This experience does not appear to square with the message I'm getting here of "just be honest about it."
As per @pixmedic 's point about offering suggestions rather than "berating" (PS - I was not berating, but rather simply addressing the issue of why that text might have offended the model), I would suggest making the conversation part of your initial pitch rather than trying to get models you already know to show more and more skin.
When you are trying to broach the subject with someone you've already worked with, it makes it feel kind of like a bait-and-switch - like this was your motive all along, to just get more cleavage. If that's not what she expects, then it can be very off-putting.
Even if it's the first time working with a model, don't wait until the shoot is already arranged before the conversation comes up. If these things aren't discussed before the shoot, it can be unnerving to be asked about undergarments. The model might be asking herself why it even matters if she is wearing a bra, and then wonder what ultimately she might be asked to do during the shoot. "Was this the plan all along, to get me to show cleavage?"
How about introducing the topic explicitely: "What are your boundaries/what is your comfort level when it comes to more revealing outfits during a shoot?" This way it sounds not like a, "Hey, how can I get you to show more skin?" to "Tell me your boundaries so I can respect them and work within those boundaries so I don't unintentionally make you feel uncomfortable." Don't make the conversation about what she is sort of willing to do or tolerate, but about the her comfort zone and boundaries. "There are times when I might want to see how an outfit or a pose looks if the clothes are more revealing. Please let me know if this is something you are comfortable with, and if not, then we will work with different outfits." or something like that.
All cards on the table right from the start.
And yes, I have been on the receiving end of the conversation, so it's not just inferring what someone might think about the question.