Reading students’ papers this summer, I kept stumbling over their use of less for fewer. But it is not a typically Dutch error (as I have to see it in my role as their teacher), nor is it new. For a paper I’m writing for the 5th late Modern English Conference at Bergamo, later this month, I analysed a very early American usage guide, 500 Mistakes of Dayly Occurrence (1856), and the problem is already included there. I still have to check our HUGE database to see if earlier occurrences can be found, but I wouldn’t be surprised if they do.
Interestingly, Peter Tudgill, too, recently paid attention to the issue, in a column he wrote for the Eastern Daily Press (22 July 2013). It should be just readable in the image he allowed me to reproduce here. Comments welcome, as usual.
Bridging the Unbridgeable 
Interesting article! I can’t remember that I ever used ‘less’ instead of ‘fewer’ but I might have done it without being aware of it ;) I wonder how old this “mistake” is…
I don’t think it originated as a mistake so much as variable usage, which normative writers like the anonymous author of 500 Mistakes of Daily Occurrence tried to define as correct or incorrect. I only called it an error from my perspective of a teacher: I have to make students aware of the fact that (in writing at least) this is a sensitive issue.
And as a usage problem it is as old as the usage guide tradition: we first find it already in Robert Baker’s Reflections on the English Language published in 1770.
It’s interesting that he presents the prescriptive rule as a singular/plural distinction. The only other place I’ve seen it put that way is Garner’s Modern American Usage. Everyone else seems to treat it as a count/noncount distinction, which leads to hypercorrections like one fewer error.
Thanks very much for the interest. You will appreciate I think that there was no space to discuss niceties like count vs. non-count in the 400 words that I am allotted for these columns!
BTW, earlier columns can be seen, if anyone is interested, at http://www.norfolkdialect.com/speaking.htm
Thanks, Peter!