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From The Collaborative International Dictionary of English v.0.44 [gcide]:
Silly \Sil"ly\, adjective [Compar. {Sillier}; superl. {Silliest}.] [OE. seely, sely, AS. s?lig, ges?lig, happy, good, fr. s?l, s?l, good, happy, s?l good fortune, happines; akin to OS. s[=a]lig, a, good, happy, D. zalig blessed, G. selig, OHG. s[=a]l[=i]g, Icel. s?l, Sw. s["a]ll, Dan. salig, Goth. s?ls good, kind, and perh. also to L. sollus whole, entire, Gr. ???, Skr. sarva. Cf. {Seel}, noun]
1. Happy; fortunate; blessed. [Obs.] --Chaucer.
2. Harmless; innocent; inoffensive. [Obs.] ''This silly, innocent Custance.'' --Chaucer.
The silly virgin strove him to withstand. --Spenser.
A silly, innocent hare murdered of a dog. --Robynson (More's Utopia).
3. Weak; helpless; frail. [Obs.]
After long storms . . . With which my silly bark was tossed sore. --Spenser.
The silly buckets on the deck. --Coleridge.
4. Rustic; plain; simple; humble. [Obs.]
A fourth man, in a sillyhabit. --Shak.
All that did their silly thoughts so busy keep. --Milton.
5. Weak in intellect; destitute of ordinary strength of mind; foolish; witless; simple; as, a silly woman.
6. Proceeding from want of understanding or common judgment; characterized by weakness or folly; unwise; absurd; stupid; as, silly conduct; a silly question.
Syn: Simple; brainless; witless; shallow; foolish; unwise; indiscreet. See {Simple}.
From WordNet (r) 2.0 [wn]:
silly
adjective
1: pungent adjectives of disesteem; "gave me a cockamamie reason for not going"; "wore a goofy hat"; "a silly idea"; "some wacky plan for selling more books" [syn: {cockamamie}, {cockamamy}, {goofy}, {sappy}, {wacky}, {whacky}, {zany}, {unreasonable}]
2: lacking seriousness; given to frivolity; "a dizzy blonde"; "light-headed teenagers"; "silly giggles" [syn: {airheaded}, {dizzy}, {empty-headed}, {featherbrained}, {giddy}, {light-headed}, {lightheaded}]
3: inspiring scornful pity; "how silly an ardent and unsuccessful wooer can be especially if he is getting on in years"- Dashiell Hammett [syn: {pathetic}, {ridiculous}]
4: dazed from or as if from repeated blows; "knocked silly by the impact"; "slaphappy with exhaustion" [syn: {punch-drunk}, {slaphappy}]
noun: a word used for misbehaving children; "don't be a silly" [also: {silliest}, {sillier}]
From Moby Thesaurus II by Grady Ward, 1.0 [moby-thes]:
154 Moby Thesaurus words for "silly": Pickwickian, absurd, airy, apish, asinine, balmy, batty, bedazzled, befooled, beguiled, benumbed, besotted, blockhead, bonehead, booby, brainless, buffoonish, catchpenny, childish, clod, clot, cockeyed, crazy, credulous, daffy, daft, daze, dazed, dazzled, dippy, dizzy, dolt, dope, dopey, doting, drip, dumb, dummy, dunce, empty, empty-headed, fatuitous, fatuous, featherbrained, flaky, flighty, flimsy, fond, fool, foolhardy, foolheaded, foolish, fribble, fribbling, frivolous, frothy, fuddled, futile, gaga, giddy, goofy, goose, groggy, gulled, harebrained, idiot, idiotic, idle, ignoramus, ignorant, illogical, imbecile, imbecilic, in a daze, inane, inept, infatuated, insane, irrational, irresponsible, jackass, jerk, knocked silly, kooky, laughable, light, light-headed, loony, ludicrous, mad, maudlin, mazed, moronic, muzzy, nerd, nincompoop, ninny, nitwit, nitwitted, nonsensical, nugacious, nugatory, numskull, nutty, off, otiose, pointless, poppycockish, preposterous, puerile, punch-drunk, punchy, rattlebrained, ridiculous, risible, rubbishy, sappy, scatterbrained, screwy, senseless, sentimental, shallow, silly Billy, silly ass, simpleton, skimble-skamble, slaphappy, slender, slight, stunned, stupefied, stupid, superficial, thoughtless, trashy, trifling, trite, trivial, twaddling, twaddly, twit, unintelligent, unreasonable, unwise, unwitty, vacuous, vain, vapid, wacky, weak-minded, wet, windy, witless, woozy
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