Top Definition
A cautionary platitude expressing the frustrations and/or ambivalence towards a situation; an exclamation of humanity's futility in the face of insurmountable insanity, stupidity, or all-around wretchedness.
- Do you ever have one of those days when you can't begin to justify having gotten out of bed?
- I'd wear a hat on a day like that!

- Kevin's coming back from vacation on Monday, and he will be pissed!
- Wow, I'd wear a hat on a day like that!

- Hey Jerry, how's it going?
- Ugh, I had an 8:30 meeting with Bill yesterday.
- Ooof, I'd wear a hat on a day like that!
by Drew Garrison February 22, 2007

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