If you are leery of something, you are cautious and suspicious about it and try to avoid it. Executives say they are leery of the proposed system They were leery about investing in a company controlled by a single individual. = wary
disapproval If someone looks or smiles at you in a leery way, they look or smile at you in an unpleasant way, usually because they are sexually interested in you. a leery grin. careful in the way that you deal with something or someone because you do not trust them = wary leery of (Perhaps from leer ; LEER)