>>38610924Skyla has tits and shows more skin. It also helps that her passion for flying is specifically in having a hobby in aeronautics in the anime. She isn't a calm, cool headed person and is kind of a hot-shot at times so that alone leaves an impression.
Winona doesn't have much behind her and is a by the books Gym Leader in the anime. A lot of the stuff Special did to define her feels pasted on.
ORAS tried to differentiate her from Skyla in that she romanticizes the act of flight but the means aren't by vehicles or devices and suggests she likes the freedom of of the skies themselves which is why she can be seen at tall structures. If one doesn't mind obstinate characters like Cynthia, I suppose that's fine but probably needs more fanart showing her feminine side.
