In English literature one thinks of Donne when thinking of the term “wit.” Critics such as Dryden, Johnson and Eliot, each using his own approach, have all commented on wit and Donne’s wit. Contemporary literary criticism, nevertheless, seems to have ignored how Donne’s own contemporary coterie critics considered “wit” and Donne’s wit. This essay focuses on John Hoskyns’s idea of “wit” and related subjects found in his Direccons for Speech and Style. Hoskyns’s seventeenth-century literary tastes give us a glimpse of how an intellectual of the time who had a similar Inns-of-Court background like Donne’s might have looked at wit and the use of wit. Hoskyns’s critical opinions are scrutinised and employed to discuss two of Donne’s early Elegies: “To his Mistress going to bed” and “Jealousy.”