miserable/ugly as sin
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(as) miserable as sin
Extremely unhappy, depressed, or wretched. Everyone just stood around looking miserable as sin during the ceremony. I felt as miserable as sin because of the breakup, but I was going to be best man at my brother's wedding, so I had to pick myself up and dust myself off.
(as) ugly as sin
Extremely visually displeasing or unattractive. This old car is all beat up and ugly as sin, but it's still going strong after all these years. I'm sure I looked as ugly as sin by that point, with my makeup smeared all over the place and my hair a total mess.
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.
*ugly as sin
Cliché extremely ugly. (*Also: as ~.) Why would anyone want to buy that dress? It's as ugly as sin! Harold is ugly as sin, but his personality is very charming.
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs. © 2002 by The McGraw-Hill Companies, Inc.
ugly as sin
Physically or morally hideous, as in I can't think why she likes that dog; it's ugly as sin. This simile, first recorded in 1801, replaced the earlier ugly as the devil.
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
ugly as sin
If someone or something is as ugly as sin, they are very ugly. Even his kids were ugly as sin.
Collins COBUILD Idioms Dictionary, 3rd ed. © HarperCollins Publishers 2012
(as) miserable/ugly as ˈsin(spoken) used to emphasize that somebody is very unhappy or ugly: He arrived at the party looking as miserable as sin. ♢ Some babies are as ugly as sin at that age.
Farlex Partner Idioms Dictionary © Farlex 2017
ugly as sinverb
See as ugly as sin
McGraw-Hill's Dictionary of American Slang and Colloquial Expressions Copyright © 2006 by The McGraw-Hill Companies, Inc. All rights reserved.
ugly as sin
Hideous, either physically or spiritually. This simile appears to have replaced the earlier ugly as the devil, mentioned by Daniel Defoe in his History of the Devil (1726). The first appearance in print was in Maria Edgeworth’s Popular Tales of 1804: “Why, she is ugly as sin!”
The Dictionary of Clichés by Christine Ammer Copyright © 2013 by Christine Ammer