I just wanted to share that you don't have to be "traditionally beautiful" to be considered a woman. I am a woman. I am aware I don't conform to society's vision of a woman. But I am a woman.
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Ok, I'm glad!
I can definitely relate to wanting to wear a style you think/know you can't pull off, but also know that we're generally our own worst critics, seeing things about ourselves others would never notice, so it's a balancing act between wearing what makes you happy and not pushing yourself too far that you then feel uncomfortable just to fit an image you have in your head (I won't even go in to what creates these "ideal" images in our minds in the first place).
One tip I got years ago that has fixed many outfits for me - choose top or bottom to be the focus point, so if you're wearing a fancy skirt, pair it with a more subtle top, or if it's a sexy top, pair with more subtle bottom, that way it doesn't become "too much". With that in mind, maybe try short shorts with a slightly longer more flowing top? Or a crop top with some high waisted jeans? I could definitely see you working a halter top, you've got the collarbone for it.
Anyway, sorry for the unsolicited advice.. ๐