I'm surprised this isn't listed as a remake of it.

To a T.

well-mannered, well-born, and thoroughly boring fiance
ditzy girl, actually smarter and more conniving than she seems
wildcat that causes any number of problems
et cetera . . .
Anyone who likes "Who's That Girl" ought to try "Bringing Up Baby" (1938). It's much funnier, Katharine Hepburn is a much better and more endearing actress, and the 1938 script takes the time to establish Hepburn's motivation: that she has designs on Cary Grant. It's so much more engaging, even in a screwball comedy, when the actions come across as intentional, rather than accidental.

The plot, yes. The character of Nikki, however, was an homage to Judy Holliday's Oscar-winning performance as Billie Dawn in "Born Yesterday".
I think it's unfortunate that the abysmal performance at the box-office clouded this otherwise funny movie that is far more successful at exuding the essence of 1950's comedies than ever was the idiotic 90's remake of "Born Yesterday" (too painful to watch, avoid it at all costs) I also think it's very unfortunate that Madonna's knack for channeling Holliday's brilliant performance was entirely ignored because her (Madonna's) public identity was so heavily confused with her stage persona. i.e. people probably didn't think the character was much of a stretch for her, despite the fact that she is (off-stage) quite intellectual.
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I think thats what they were trying to go for.
Mecca