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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Used to indicate that the speaker is a man and currently wearing a hat.
"I am a man who is wearing a hat"
by Daniel Kogel May 8, 2007
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If a girl puts on your hat, she wants to fuck.
Bro! she grabbed my hat at that party, and I let her wear my hat... the rest was history.
by Arcenator October 19, 2011
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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
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(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
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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.
Dude 1: "Tonight my friend, I shall wear the fox hat."
Dude 2: "Yo Dawg! Way to go, my man."
by Wizards Sleeve March 4, 2007
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