I have this headcanon that femm!Dean would be incredibly stunning and she knows it and she likes flaunting it, although there are days (or weeks) where she foregoes bathing and putting on nice things for a hunt or just to stay in and recoup from a hunt gone bad. She has this constant inner debate between being masculine enough for John - strong enough to protect her loved ones, being a genius mechanic, handling a gun just as well, or even better, than her dad - versus being feminine - indulging in her love of cooking, fixing up her hair, shopping for the best suits/dresses. Later on, she learns that the battle between what she considers her masculine vs her feminine features is completely moot; she learns to accept that all those - her mechanical prowess, her accurate shots, her great lasagnes and fashion sense - are neither more masculine or more feminine than the other, but that they are all a part of her. There’s no debate, no battle - just a whole host of things that make her awesomely kick-ass.
You headcanon this for femm!Dean? You just described almost exactly how I interpret DEAN Dean :) Also OMFG BEAUTIFUL ART!