Thomas, Mathew, and Robert Hale are most likely grandsons of Simon att Hale. The three brothers are mentioned in their cousin William at Hale's will from 1520.
I suspect that Robert is the father of the Arnold Haile, gentleman, who appears in Frinsted's christening records between 1566-74. The statement that he was a "gentleman" would seem to confirm an alleged descent from the Hales of High Halden.