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.
wear the bull's feather
To have an adulterous wife; to be cuckolded. The cuckold is traditionally associated with horns, and a "bull's feather" was once a term for a horn. I never thought I would wear the bull's feather, but it's true—my wife cheated on me.
wear the cap and bells
To provide humor and merriment (sometimes by acting as a target for mockery). The phrase refers to the hat adorned with bells that court jesters once wore. Sean will wear the cap and bells—you can always count on him to liven up a party. I guess I'm wearing the cap and bells today because they are having a great time ridiculing me.
wear the horns
To have an adulterous wife; to be cuckolded. The cuckold is traditionally associated with horns. I never thought I would wear the horns, but it's true—my wife cheated on me.
wear the willow
To grieve. The willow tree is traditionally associated with sadness. My grandmother has been wearing the willow ever since my grandfather died. I wore the willow after my true love married another man.
wear several hats
To hold or function in more than one position or role. I work from home, so I'm able to wear several hats: stay-at-home dad, soccer coach, and website developer. Both our editorial assistant and our copywriter left the company at the same time, so I've been wearing several hats ever since.