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I have a colleague of whom this is a favorite phrase, used in the sense of "knock yourself out", "go for it", "have at it", "go to town", "help yourself". ("You want to add that feature to the software? Go ahead - fill your boots!")

So far, the best origin story I've heard is that of "when plundering, using every available container - i.e., even your boots". It feels as though there may be more to it than this, but I've not discovered it yet. What say?

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I don't recognise the phrase. Perhaps it is just your colleague's personal expression? – Colin Fine Dec 20 '10 at 18:06
I haven't heard of it either, but I'd guess it means something like "Get your boots on and get going!" – mmyers Dec 20 '10 at 20:04
Well I've heard it all my life in London. Usually used negatively in my experience, in the same manner as "help yourself" when said flippantly. – Orbling Jan 1 '11 at 7:14

5 Answers

A quick search yielded

At the HMS Victory museum in Portsmouth UK, you can buy a thick leather cup lined with pitch. This is a replica of the sailor's mug used on board in Nelson's time, and it was used (among other things) for the rum ration when issued. This cup is called a "boot", and when things were good and you got an extra rum ration, sailors were told "Fill Yer Boots"!

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2  
Incidentally, I've always heard this phrase pronounced as above, yer, in that 18/19th century naval twang. Saying it fully with your sounds wrong. – Orbling Jan 1 '11 at 7:18

As all good sayings do, it comes from a sailor.

The following is an excerpt from Memoirs of Serjeant Paul Swanston: being a narrative of a soldier's life, in barracks, ships, camps, battles, and captivity on sea and land; with notices of the most adventurous of his comrades. (no, that's really the full name of the book), first published in 1818.

In quick time they were at the wine-pipe; for a moment the new hands seemed at a loss for the means of getting the wine to their mouths; but the "wide-a-awake" boy sliped (sic) off one of his shoes in a twinkling, dipped it into the cask and drank.

"Drink, you devils, drink!" he said; "its all one how much you drink, only don't get drunk!" And again he filled his shoe, and again he drank. The previous debauch in connexion with the new, soon tumbled him on the ground; and he lay there gradually sinking into stupidity; but, as he took his leave of consciousness, he admonished the others to take care of themselves; to take as much as they could rightly carry; but not to get drunk, saying, as he sunk lower and lower himself, "Fill your boots, boys—fill your boots! Give me one small drop in a shoe to make me well again, for I'm— I'm—."

Alas, poor humanity! There lay in the deepest degradation, as good a fighting soldier, and, when he could not get drink, as cleanly and active a fellow as ever the English army possessed.

I can't think of anything more exemplary of gusto than a sailor getting blind stinking drunk out of his shoe.

You can read the full text here.

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I don't think the Memoirs of Serjeant Paul Swanston is really 1818, Google often has bad metadata. Wikipedia gives it as 1840, which makes more sense than 1818 given the author Alexander Somerville's lifespan (1811 – 1885). / Google Books just gives a snippet for me, here's the same scanned book in full from the Hathi Trust. – Hugo Feb 19 at 14:29
This is an account of sailors literally using their shoes or boots to drink from, and it's strange I can't find any other 19th century examples of sailors using the phrase literally or figuratively. – Hugo Feb 19 at 14:42

english coal miners wore hobnailed boots which were slippy on cobblestone streets, so they carried them home after work so they wouldnt slip. this allowed them to "fill their boots " with coal which would be just enough coal for a family for one day.considered one of the perks of working in a coal mine.

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Do you have any references for this? – Hugo Feb 19 at 8:48

Urban Dictionary has an entry dating from 2005:

http://www.urbandictionary.com/define.php?term=fill%20your%20boots

Google reveals a number of references to the phrase, including a punk rock album title. I can't find any definitive reference, but the explanations seem to center around the Cavaliers, boots, and the usual horse-hockey you find in etymology.

I think the common-sense explanation you've arrived at is probably the right one.

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"Fill your boots" was an order given by William of Orange to his troops before the Battle of the Boyne. The boots refered to leather water carriers that each soldier had strapped to his saddle.

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