Taking a sociolinguistic approach to prescriptivism in English usage, this article presents different methods by which highly frequent usage problems can be analyzed as to their current acceptability. These methods comprise different ways of studying a selected number of well-known items—try and/try to, the placement of only, the split infinitive and the dangling participle—focusing on their treatment in British and American usage guides from the beginning of the prescriptive tradition onward, combined with the application of special elicitation techniques to probe the views of informants. Such a multi-modal approach represents a distinct improvement from earlier attempts at presenting targeted groups of informants with attitude surveys only. By studying representative samples of British and American usage guides, the article shows that attitudes became more lenient across time (though not for all usage problems analyzed), with the sociolinguistic variable age playing an important role in the process, but also that instead of usage guides becoming more descriptive in the course of the history of the tradition, today in effect two trends can be distinguished in the type of usage advice given. While one trend indeed shows an increasingly descriptive approach to the items treated, a continuing proscriptive approach characterizes usage guides published down to the beginning of the 21st century.