Unfortunately I think this is one of those things that when the young kids do it, it looks hip and cool, but when women of a certain age who are old enough to have young kids who look hip and cool do this, they look like they are wearing orthotics.
I say this as one of those “women of a certain age!”
Unless you’re Helen Mirren, in which case, you go.
That being said, I did get a pair of these, inspired by Helen Mirren, although I haven’t worn them with dresses (yet, everything is a muddy mess and I don’t want to muck up my new shoes!)
https://www.instyle.com/fashion/helen-mirren-oca-low-cariuma-sneakers