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!
- 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
"I am a man who is wearing a hat"
by Daniel Kogel May 08, 2007
by Arcenator October 19, 2011
He wears a green hat, if you know what I mean.
by ggigii September 02, 2007
Meaning working in the yard or garden. Comes from the fact that farmers when working in their fields used to wear straw hats.
by Otto Von Coop November 11, 2010
(phrase) Sounds innocent enough, but say it with an Irish accent and people might think you've just said "where the fuck's that".
American wearing a fox hat: When I told the folks back home that I was coming to Auchtermuchty, they said, "Wear the fox hat!"
by EqualsPeach October 29, 2017
Having a woman sitting on your face. A woman with a very large hairy bush. And if she is a red-head, it is a perfect fox hat.
by Wizards Sleeve March 04, 2007