fill your boots

what is the origin
17:40 Wed 16th May 2007
 
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The idea of ´┐Żfilling your boots' almost certainly dates back to the days when a victorious army would plunder the places they had recently attacked and defeated. Obviously, the soldiers would stuff their pockets, saddle-bags or whatever and then - so as not to miss anything - even their boots with booty...if you'll forgive the choice of word! Soldiers - particularly cavalrymen - in past times often wore wide thigh-length boots which were quite roomy! That's why we have the modern sense of "take full advantage" when we use the saying.

We see a more modern version of the same idea in the word ´┐Żbootleg', coined in America to describe illicit goods - ie things you would have to hide - especially alcohol. This meaning relates to concealment rather than taking advantage.
Any chance the expression could be an alternate to "fill your shoes" -- as in, "We're sorry you're stepping down as committee chair. It will be hard to find someone to fill your shoes."
In that sense, it means "be a worthy successor."
In British English, 'fill your boots' is invariably an instruction to take full advantage of some situation. 'Fill your shoes' is invariably used in the kind of situation you describe, Kingaroo. As you say, we might find it in, "Once you've gone, nobody will ever be able to fill your shoes"...ie do the job as well as you've done.
The two are not interchangeable...at least not on this side of the Atlantic!
This one has two meanings - 1) If the person who said it is from Newfoundland, Canada, then it means to take your fill of something, like "help yourself to as much as you want". 2) If you are making refernce to someone filling their boots, it refers to what would happen if you pooped your pants severely (from a fright), it would flow down and fill your boots.

Wetting your pants and "filling your boots" after a fright - a phrase used to refer to someone who isn't very smart: "Couldn't pour p*ss out of a boot with the directions on the bottom."

http://www.phrases.org.uk/bulletin_board/7/mes sages/560.html

Exclam. Help yourself! Enjoy yourself!
Vrb phrs. Be very scared.

http://www.peevish.co.uk/slang/f.htm

Phrase "fill your boots" used to mean "have at it" or "take/do all you want", "have your fill", etc. While the phrase does have other meanings...the phrase originated with the english Cavaliers, who wore thigh-high riding boots. When drinking, rather than stepping outside to relieve himself, a Cavalier apparently had the option of doing so into his boots. Thus, "filling his boots" meant he could drink all he wanted without leaving the table.

http://plateaupress.com.au/wfw/fillyour.htm

1. Invite another to help themselves to their optimal capacity or
2. Attempt a difficult task or ordeal.
3. An invitation to partake with gusto, as in "be my guest," or "help yourself."

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

At the H
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", since boots are made with leather.
When things were good and you got an extra rum ration, sailors were told "Fill Yer Boots"!
The origin of the term predates modern history. Plato wrote about people carrying out a sexual act involving Goats and Sheep in his legend of Atlantis. He refers to Greek shepherds and Goat herders who would catch a goat or sheep, tie its back legs to their own and then perform a sex act on the animal. From which behaviour the term "Bestiality" originates. The Romans also described the same behaviour. Later when boots were worn shepherds and goatherders were seen to carch a sheep or a goat, put the animals back legs into their boots and perform a sex act on the animal. There are records in magistrates courts along the following "I saw him catch the animal and fill his boots with its back legs. He then inserted his erect member into the rear of the animal and move about. Sometime later he removed his member and released the animal." Polite society refused to acknowledge that such perverted behaviour did occur.

It has in more recent times come to refer to the habit of people usually males looking for sex to enter an establishment where women often prostitues are known to frequent and an often used term is "Would you like to fill my boots for me?" It is used as a covert terminology for sexual favors involving prostitues, lesbians and gay men when in more genteel society.

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