Etymology
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seamy (adj.)

c. 1600, "least pleasant, worst," literally "having a seam or seams," but here especially "showing the seams," in the figurative phrase seamy side, from seam (n.) + -y (2). The seamy side of a sewn garment is less attractive and is typically turned in. The popularity of the figurative sense likely is due to its use by Shakespeare: "turn'd your wits the seamy-side without" ["Othello" IV.ii.146]

updated on March 15, 2022

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Definitions of seamy from WordNet

seamy (adj.)
showing a seam;
seamy (adj.)
morally degraded; "sleazy storefronts with...dirt on the walls"- Seattle Weekly; "the sordid details of his orgies stank under his very nostrils"- James Joyce;
the seamy side of life
Synonyms: seedy / sleazy / sordid / squalid
From wordnet.princeton.edu, not affiliated with etymonline.