Having been taught the grammatical rule viz. the usage of ‘fewer’ and ‘less, and being aware that signs at checkouts in shops such as “five items or less” are technically incorrect, I want to ask the following question:
First, should it be “£5 or less” or “£5 or fewer”? And, secondly, if the answer be ‘fewer’, is it correct then to say “half price or fewer”?
Thank you,
Saint Anthony.
Ora pro nobis, sancte antonie!
The correct usage is that fewer is proper when enumerable discrete objects are referenced, and less when a measurement out of an unenumerable quantity is being discussed. One speaks of “fewer than twenty surviving Javan rhinoceroses” because one can go count the number of rhinos that survive in that game preserve. But one says “less than five pounds of sugar” because sugar does not come in neat one-pound quanta – one may have 4.995 pounds, three pounds, or 1.067 pounds and still be accurately speaking of the quantity.
As you note, “Fewer than 12 items” would be accurate, but “less than $5.00” (forgive my converting to U.S. currency, but I don’t want to go looking for the pound-sterling sign) is correct because “money” is conceived of as akin to substance rather than discrete units of currency. Just as you may have a one-pound, five-pound, or ten-pound tin of coffee, you may have $1, $5, or $10 notes. And just as you may take a small scoop out of your coffee tin, you may break a dollar into petty change.
FWIW, one of the local grocery chains (Farmer Jack) has signs that strike me as strange every time I see them: “12 items or fewer.” It’s strange to me because of its correctness; it seems out of place in a grocery store where the horrid “less” seems to be omnipresent.
However, would it be “fewer than five of your American dollars?”
Unless I’m mistaken it is just the opposite of much/many. The coorect choice depends on whether the answer to a question requires qualification.
How much gas do I need? Five gallons.
How many apples did I buy? Twenty.
How much gas do I need? Less than 5 gallons.
How many apples did I buy? Fewer than 50.
So if no descriptor or measure is required it’s many and fewer.
Only if Leslie Charteris wrote it. But grammatically I think that is quite right, old chap.
Isn’t there a rule about quoting one Saint to another? 
The way I explained it to my children was that fewer and less had the same relationship as boogers and snot. If you can count them, they’re boogers, but if you have to weigh it, it’s snot.
Yes but:
How MANY dollars?
Therefore, 5 or fewer?
According to Bryan Garner’s A Dictionary of Modern American Usage, which is one of the best of its type:
£5 or less.
Half price or less.
In cases where the ‘correct’ term is a close call, you may be doing yourself a favour by using an alternative construction if it is just as clear or clearer. Sometimes, it’s best to just say ‘not more than five pounds’ and be done with it.
These quotes look weird with only the top and left borders. Or am I doing something wrong?