@Strangelovekraft
I honestly feel uncomfortable being "the authority" in this discussion, as I'm a white girl, 😉 but I'll do my best. Also, I've heard PoC say that it's annoying that they always have to be the ones to do the educating! so hopefully I won't screw it up...
Yes, many black communities have beautiful head scarf traditions! especially in Africa. In Louisiana, they had the Tignon Law requiring African-American women to cover their hair with a scarf, and many of these women made gorgeous hair coverings and wore them with pride. So no, not all head scarves are racist!
On the other hand, yeah, if you do a google image search for "Mammy" or "Aunt Jemima" you get a lot of stereotypical images of full-figured, dark-skinned women wearing very utilitarian headscarves and you know, the way these stereotypes work is you know it when you see it? and you're more sensitive to it if it's been used against you. ☹️
So, in short:
Yes! there are absolutely African-American women who wear a head scarf with pride!
No, I'm not going to invalidate the OP's feelings about this outfit. Again, you know it when you see it, and they would know better than I would! I'm not trying to talk over the OP, just remove some of the "It's not their job to explain how racism works while complaining something is racist" burden, and we should listen to the Simmer of Color as the authority.
I hope that helps!