sweetly or innocently charming; winning; engaging: a winsome smile.

before 900; Middle English winsom, Old English wynsum, equivalent to wyn joy (see wynn) + -sum -some1

winsomely, adverb
winsomeness, noun
unwinsome, adjective Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
winsome (ˈwɪnsəm)
charming; winning; engaging: a winsome smile
[Old English wynsum, from wynn joy (related to Old High German wunnia, German Wonne) + -sum-some1]

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
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Word Origin & History

O.E. wynsum "agreeable, pleasant," from wynn "pleasure, delight" (cf. Ger. Wonne "joy, delight;" see win) + -sum "-some." Apparently surviving only in northern English dialect for 400 years until revived 18c. by Hamilton, Burns, and other Scot. poets.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
To-day it was the winsome one, bringing always flowers as sweet as herself.
But the future of these winsome primates is in doubt.
Reading vintage bartending manuals can be a winsome treat.
Now it is time to celebrate the saucy little street urchins, the winsome
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