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wear rose-colored glasses
To assume an unduly optimistic and cheerful attitude (toward something); to focus solely or primarily on the positive aspects (of something). Primarily heard in US. Many of us wear rose-colored glasses when we think back to our childhoods. It's part of the reason nostalgia is such a powerful emotional draw. I find it a little irksome how you always wear rose-colored glasses, even in the worst of times!
wear sackcloth and ashes
To act in a way that shows one's penitence or remorse for one's misdeeds or poor behavior. Darren has been wearing sackcloth and ashes ever since his girlfriend broke up with him for cheating on her. There's no way to turn back time on the way I treated my brother growing up. All I can do now is wear sackcloth and ashes.
wear too many hats
business slang To hold too many responsibilities or assume too many roles at the same time. One of the pitfalls many entrepreneurs fall into when setting up a new company is to wear too many hats, which not only spreads themselves very thin, but ends up being counterproductive to the operation as a whole.
be wearing your [teacher's/lawyer's etc.] hatalso have your [teacher's/lawyer's etc.] hat on
to be acting as you do when you are working as a teacher, lawyer etc., which may be different from the way you act in other situations I was wearing my teacher's hat at the meeting.
wearing (nothing but) a smile
tv. naked. This doll came on stage and within ten minutes she was wearing nothing but a smile.