How can I reassure her?

Anonymous
I'm dating a girl off & on that I've been friends with for 25 years.. Except for when she got a little heavy for a while, her preferred style of dress has always been tucked in blouses & tops. I particularly like to see HER tuck things in because that style is so much a part of her! Well, a while back she was hitting the gym & started tucking tee shirts into fitted shorts as well, & I thought it was BEYOND HOT, but if she tucked ANYTHING in her mom would be mean & say, "Tuck that out! You look like a FAT PIG!" She'd cry & ask me if she was really that UGLY & FAT and needed to pull out her shirts, so I started encouraging her to tuck them in, wanting her to feel good about herself. I guess I went overboard because she got like, I get the message... You want me to tuck it in, I'll tuck it in, I don't care... I apologized & kind of dropped it. Fast forward 20 years, she sees a friend in a tucked in uniform (By the way, the girl is like a sister & dependent on me for transportation...) who hates tucking in anything, but hadn't bothered to tuck it out yet after work, but because the girl was technically "outside" work, my girlfriend was like, she cuter, she tucked in her shirt, she looks better with her shirt tucked in, you want her... I reassured her that my friend was just a friend & she HATES to tuck in ANYTHING, but a few weeks later my Girlfriend will start again, when she's the one who ACTUALLY tucks in everything! I've gotten calls while waiting for my friend to come out of work like, "You're they're early hoping to see her before her shirt gets pulled out!" How can I get reassure her & get her to put this to bead after 20 years of this? What was the alternative? I couldn't just watch her cry & be forced to dress a way that made her feel ugly...
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Wow, I didn't expect this question to get so many hits... I'm not complaining though, thanks for the help! :)
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link OK, this is kind of how she dresses, though sometimes dressier... She's also a little more full figured, but not fat just BIG FRAMED! For her, 165 is rock solid no fat...
How can I reassure her?
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