Definitions
American Heritage® Dictionary of the English Language, Fourth Edition
- adj. Entirely without money.
- adj. Very poor. See Synonyms at poor.
Century Dictionary and Cyclopedia
- Without a penny; moneyless; poor.
Wiktionary
- adj. Not having a penny; utterly impoverished; extremely poor.
GNU Webster's 1913
- adj. Destitute of money; impecunious; poor.
WordNet 3.0
- adj. not having enough money to pay for necessities
Etymologies
- penny + -less (Wiktionary)
Examples
“It was natural, therefore, that he should have objected to your father's engagement to what he called a penniless governess.”
“That's true in a strictly financial sense, but I think most human beings would feel that the work of a man who spends his life inoculating the penniless is worth more than the work of the man who tends to Paris Hilton's little dog.”
“#20 - I agree that making single mothers homeless and penniless is not the answer.”
“Like Donna Elisa, every one in penniless Diamante had decorated along the whole street.”
“If you’re so smart (cause a tragedy which leaves YOU penniless is SO unlikely to occur – “God can’t touch you, eh?”), why don’t you run for President?”
“He was what the world calls penniless, having an income from his father just sufficient to keep him like a gentleman.”
“1492: Jews were given the choice of being baptized as Christians or be banished from Spain. 300,000 left Spain penniless.”
Think Progress » BREAKING: Military Will Request $100B For Iraq Next Year, Murtha Reveals
“Instead of weeping over the sad situation of his "penniless" mistress and showing any signs of contrition for having wronged the man who held the mortgage of seven hundred and fifty dollars on him, James actually”
“It is hard enough to make a living without having the Kelly’s of the world suddenly decide that they should, can and do make a living off of free work from others yet demand that those that provide them with their income remain penniless.”
Facebook Members Sell Their Own Ads - Bits Blog - NYTimes.com
“It added that Jacobs died "penniless" in a London hospice in”
Lists
These user-created lists contain the word ‘penniless’.
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-more or -less
Words ending with *more or *less, more or less. Many of theses terms also appear on the list The -less Said, which see.
schemaless, unless, useless, guileless, wireless, regardless, homeless, endless, nevertheless, countless, jobless, doubtless and 434 more...
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My Self-Descriptors: A Mirror of Text
Read this list, and read it well. When you finish, you'll know me better than my mother. That is, unless she reads this list too.
libertarian, unorthodox, unfinished, sincere, frugal, lanky, introspective, critical, laid-back, taciturn, lexiphilic, kindly and 115 more...
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The -less Said...
hopeless, bootless, groundless, luckless, artless, feckless, hapless, joyless, useless, penniless, childless, peerless and 310 more...
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wordsmithing part deux
because wordsmith is not a verb.
enmity, incarnate, chignon, nape, solitude, nocturne, decorum, warren, svelte, interstice, serene, charlotte and 488 more...
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me + student loans =
You know that feeling when you open your wallet and all you can find inside are ATM receipts?
When being a squatter is the least of your worries and that thing called dignity is shove...destitution, beggary, impecuniosity, indigence, mendicancy, poor, impoverishment, pauperism, pennilessness, penuriousness, penury, poverty and 168 more...
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Kerouac
Words from Kerouac's work.
joual, passaic, quirt, fellahin, hoorair, hincty, vag, orgone, huzzahed, idjit, shroudy, forgather and 17 more...
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Triple Doubles and Other Multiples
inopportune, poussette, clapperless, shoelessness, didgeridoo, sheesh, storyteller, frontierless, slaughterhouse, enfeoff, plantagenet, blunderbuss and 36 more...
Tweets
Looking for tweets for penniless.

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