A hat that's permanently worn in public by men in their 20s and 30s that are going bald, but aren't ready to show the world that they're bald.
Person 1: "I haven't seen Larry without a hat in 5 years."
Person 2: "It's his comfort hat. He's not ready to show the world that he's bald"
Person 1: "He should just go bald sometimes without a hat. Bald is beautiful."
person 2: "He should be like Jeff and just accept that he's bald. Jeff doesn't wear a comfort hat. Sometimes he wears a hat--but he also goes out in public bald and hatless."
Person 2: "It's his comfort hat. He's not ready to show the world that he's bald"
Person 1: "He should just go bald sometimes without a hat. Bald is beautiful."
person 2: "He should be like Jeff and just accept that he's bald. Jeff doesn't wear a comfort hat. Sometimes he wears a hat--but he also goes out in public bald and hatless."
by doctorsupreme May 24, 2022

A hat that you put on on a weekend morning at college when you want to go out to eat brunch but you don't want to shower first. The hat disguises the disgustingness of your unwashed hair and gives the impression that you got dressed this morning, when in fact all you did was pull some jeans on over the boxers you slept in.
Roommate #1: Man, I'm really hungry, but I don't want to shower, or put on pants, or move at all really.
Roommate #2: Dude, just get yourself out of bed, put on your brunch hat, and go get something to eat in the dining hall. You can shower tomorrow.
Roommate #2: Dude, just get yourself out of bed, put on your brunch hat, and go get something to eat in the dining hall. You can shower tomorrow.
by Hobo Style September 8, 2013

A type of hat which doesn't quite reach the top of the ears. A Gary hat is often worn by paedophiles' or retards that can't get themselves dressed.
Chad 1: Hey chad!
Chad 2: Yo chad!
Chad 1: Oh my gawd, your hat is amazing dude!!
Chad 2: Thanks MAAAN!
Chad 1: What type of hat is it and where did you get it from?
Chad 2: I got it from Gary World and it's name is a Gary hat.
Chad 1: I'm asking my mom for that. ITS RAADDD!!
Chad 2: Yo chad!
Chad 1: Oh my gawd, your hat is amazing dude!!
Chad 2: Thanks MAAAN!
Chad 1: What type of hat is it and where did you get it from?
Chad 2: I got it from Gary World and it's name is a Gary hat.
Chad 1: I'm asking my mom for that. ITS RAADDD!!
by Ashton & Chris February 16, 2022

The instance when your dick is trying to enter a busted up vagina and the flabby labia fold in on the vaginal entrance so your dick can't get in but is just hanging out wearing a "sad hat" of floppy pussy folds.
Last night I was hanging with that ho Jessica and when we tried to have sex, I couldn't get my dick in her pussy cuz those nasty meat curtains just folded up on my dick like a sad hat.
by Taintamount December 2, 2016

by that is ridiculous August 21, 2006

The Hat Man knows all, The Hat Man sees all. And he wants to meet you. To summon his physical form to our Plane of Existence, you must perform the ritual. First, place a Tophat of your choice on the floor, and cover the ground around it with garlic salt. And then light the salt. Once that is completed, you must consume a high enough dosage of a drug to induce a high feeling. And then sleep laying next to the ritual. At exactly 3:45 am, you will awake, and The Hat Man will be there to visit you.
by The Hat Man__ January 17, 2023

A gaudy hat worn to church. Frequently incorporate sequins and/or bows. Generally have matching gloves. Most commonly seen on the heads of middle-aged+ black women in the South on Sundays or at any other formal occasion.
by 241405 January 23, 2009
