It is so tough to find a shape to balance out that much hair. Your look starts off so dramatic at the top and finding volume for the bottom while not looking busy is hard. (I know from personal experience.) I think the skirt is great with the airy heels, even better, and an adventurous bag is the right decision. Just maybe not this bag, maybe something slightly smaller with more colour.
PS Maintaing that volume at the roots of her hair, takes serious committment to personal style. Fab to see that discipline for a style most people think is so effortless.