British slang, now mostly historical, meaning flat broke, skint, or seriously short of cash. If you're oofless, your wallet is empty and your bank account is painful to look at. The word derives from 'oof', which was Victorian-era slang for money. Being oofless was the natural opposite — having none of the stuff. While the term has faded from everyday use, it's a colourful piece of old London English with a pleasing ring to it.
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UK and Irish slang — Cockney, Scouse, Geordie, Yorkshire, Glaswegian, Brummie, Welsh, West Country, plus Irish English. Centuries of regional dialects feeding into modern British and Irish street talk.
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Can't come to the pub tonight, mate — completely oofless until payday on Friday.
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(UK, slang) Short of money; poor.
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