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All I know is that it's old. 
Wiki says the first written occurrence of it was in Francis Van Wyck Mason's novel, Spider House, published in 1932.
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Does this come from a saying or something? The only thing I can think of is someone saying "cold as tits" >

Cold as a witches tit in a brass bra >

Is this a real saying? Is this some regional thing or something? >

I've lived in multiple parts of the U.S. and it's very common >

I’ve never heard this. Grew up in NY and live in Colorado. I don’t think it’s as common as you think it is. >

Colder than a witch's tit with a brass bra. 
It's 100% a saying that exists. I've lived in Colorado, Alaska, Ohio, Washington, Arkansas, and California. It's more prominent a saying in the Midwest, but it used to get a giggle or nod before people decided to make every damn word an issue. 
Look, nobody is hating witches here, just that in a brass bra, their tits are cold. >

Oh i never said it didn't exist.  I just said it's not as common as people think it is.  I'm 36 and have never heard it before today. >

Weird. I'm 32 and I've heard it everywhere. >

I have never heard the brass bra part, just the colder than a witch's tit. Mostly California, and some TV media. >

I’m sorry what? Witch’s breasts? What the hell is this? I have never heard anyone talk about a witch’s breasts before. >

As cold as a witch's tit in a brass bra on the shady side of an iceberg >

Never heard that >

I can most assuredly say that today is definitely colder than a witch's tit , with a brass bra. 
You can no longer pretend it's not a saying, nor that you are uninformed that it exists. >

Have you seen what they wear on Halloween? It's not surprising they get cold. >

OK, stealing this >

Every witch's teat that I've encountered has been cold as all get out - which teats have you been sucking on? >

Who drinks warm milk? >

'Twas said that witches had a third nipple - for feeding blood to their familiars, or even the Devil hisself! I wouldn'a thought that one was cold... >

Can someone explain to me the context of this? I'll gladly appreciate it. >

I mean, have you seen witch titles? They are actually pretty hot. >

That's the power of magic. They look hot....but cold to touch. I didn't make the rules. 
Just kidding, but if I was going to try to imagine a sensical idea behind this saying, I'd imagine that maybe witches are inclined to be topless. Therefore, cold bewbs. >

I literally JUST had this discussion, how random. 
What I basically deduced is that witches are old hags, therefore they don't get any action. As a result, their tits are cold and untouched 🤷🏻‍♀️ I don't make the rules lol >

We live in a simulation >

I also like the alternate saying, “Colder than a warlock’s dick in a brass jock strap.” >

Nobody ever says this unless they are purposely deflecting. >

This is a misquoted saying originating at the turn of the 19th century in regards to well diggers.
Their practice of finding water, or "witching," was often done as a nomadic service. It was common practice for the witchers to live in Native American style teepees or...tents.
In the northern United States, their dwellings would rarely provide adequate winter coverage, so they would barter to stay in a homesteaders dwelling until they moved on. 
As it happens, "colder than a witcher's tent" evolved into what we now are accustomed to say: "colder than a witches tit."
Thank you for letting me waste your time reading this made-up fact! Happy Holidays! >

So that's why you toss a coin to them... >

I believe without evidence that this is squaddie poetry. 
An englishman only truly bares his creative muse on minimum pay, after two days awake, after being told to do something pointless by a nonentity. 
My personal favourite is being told that a piece of work I had done looked like a madwoman's shit. I still wonder how that woman is doing. >

Hahahahaha. Now I'm also hoping that madwoman is doing well. >

It's because witches wear brass bras. 
"It's colder than a witch's titty in a big brass bra" - that's the whole saying. >

I have never once heard of this saying. Is this a regional (assuming US) thing?