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I'd wear a hat on a day like that 

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!

Go Wear A Hat 

Did you just call me ugly? Go wear a hat bitch”
Go Wear A Hat by Coleshot January 24, 2020

National Wear A Squid Hat Day

On May 8th you could wear a squid hat to maybe get some laughs or maybe get some strange looks but it's all just for fun.
Dude 1: *Wearing a squid hat*
Dude 2: Why are you wearing a squid hat?
Dude 1: Because of its National Wear A Squid Hat Day
Dude 2: Oh cool *puts a squid hat on* now we are both wearing squid hats

wear me like a hat 

the act of one female sitting on the head of a male. (preferably nick haro)
Oh yeah, wear me like a hat daddy!

i would rather shit in my own jocks and wear them as a hat

to put it in layman's terms, you make me so sick i would rather defecate at the expense of my own undergarments instead of being in your presence.
your so shit that i would rather shit in my own jocks and wear them as a hat than know you!

Don't wear fire as a hat 

don't wear fire as a hat