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with suspicion, mistrust, or disapproval:
He looked askance at my offer.
with a side glance; sidewise; obliquely.
Historical Examples

Her little Ladyship, eyeing me askance, answered, ‘I can’t come now—the dress-maker is waiting to fit on my frock.’
Discipline Mary Brunton

When John Kenyon entered his office, he thought the clerk looked at him askance.
A Woman Intervenes Robert Barr

They crowded away from the two well-dressed high-school girls, looking at them askance.
Nan Sherwood at Pine Camp Annie Roe Carr

Claude, who was now growing embarrassed, had examined the girl, askance.
His Masterpiece Emile Zola

In more fashionable circles the mere possession of a pipe might be looked at askance.
The Social History of Smoking G. L. Apperson

The lanky Sucatash looked at him askance, catching the note of sentiment.
Louisiana Lou William West Winter

Lukynitch stood with his grey head bent on his breast, and stared at me askance in a strange sort of way.
The Diary of a Superfluous Man and Other Stories Ivn Turgnieff

“You speak of the castle as if you knew about it,” said the landlady, eyeing her askance.
The Old Countess; or, The Two Proposals Ann S. Stephens

At first, indeed, his activity had been looked at askance at Innsbruck, as but another force making for disintegration.
Encyclopaedia Britannica, 11th Edition, Volume 3, Part 1, Slice 1 Various

Men pretending virtues as relentless as his own were often inclined to eye him askance.
Erik Dorn Ben Hecht

adverb
with an oblique glance
with doubt or mistrust
adv.

1520s, “sideways, asquint,” of obscure origin. OED has separate listings for askance and obsolete Middle English askance(s) and no indication of a connection, but Barnhart and others derive the newer word from the older one. The Middle English word, recorded early 14c. as ase quances and found later in Chaucer, meant “in such a way that; even as; as if;” and as an adverb “insincerely, deceptively.” It has been analyzed as a compound of as and Old French quanses (pronounced “kanses”) “how if,” from Latin quam “how” + si “if.”

The E[nglish] as is, accordingly, redundant, and merely added by way of partial explanation. The M.E. askances means “as if” in other passages, but here means, “as if it were,” i.e. “possibly,” “perhaps”; as said above. Sometimes the final s is dropped …. [Walter W. Skeat, glossary to Chaucer’s “Man of Law’s Tale,” 1894]

Also see discussion in Leo Spitzer, “Anglo-French Etymologies,” Philological Quarterly 24.23 (1945), and see OED entry for askance (adv.) for discussion of the mysterious ask- word cluster in English. Other guesses about the origin of askance include Old French a escone, from past participle of a word for “hidden;” Italian a scancio “obliquely, slantingly;” or that it is a cognate of askew.

see: look askance