hope this doesn't cause any fallout 4 between us

Most "hard to draw" hats - y'all know which - ALSO fall into a very specific category. The category is:

That's right: A wide circular brim on top of a crown (or "egg stuck through portal" depending upon how you interpret the above). SO why the hell are they so complicated to draw? The answer:

...MEN.

No, really. So "the most basic hat shape" became a SUPER inconvenient style for 1700s European/colonial people men of means for two reasons:

1) it did not conveniently allow display of FANCY WIGS, which were beginning to come into fashion between the 1600s-1700s;

2) it was obnoxious to carry wide-brimmed hats around - a bit of a problem, since European societal norms dictated hat removal when a gentleman went indoors.

AND SO...the "most basic hat shape," ubiquitous in Western European cultures for some time prior, got upcycled by cocking (folding up) the brim. We first got the cavalier hat:

Related modern hats include the slouch hat/bush hat -

- and of course, your Favorite Guy's hat.

...BUT I CAME HERE FOR CHIPS

And chips you shall have.

You see that brim on Preston's hat? That's one of these (which my wife has informed me is known as a "wish chip" - I have learned something new, thank you @twosides--samecoin):

The thing to keep in mind is that, like a potato chip, this whole brim situation is just a circular plane with a hole in the middle, folded over on one side. See those shapes above? Now see them below, on the cocked side of the brim:

...WHAT ABOUT HANCOCK'S HAT

Well, around the 1700s, our male trendsetters decided it wasn't enough to turn up one brim; it needs must be Fancier™, and show More Wig, and be More Convenient With Which to Use Firearms - and we got the cocket hat (if you're Scottish)/bicorne, as well as the cocked hat (later known as the tricorne). Same circular brim, but for a tricorne, folded up thrice:

And yet again, this is just a potato chip. Observe:

See how that nice fold is acting? Now apply directly to hat:

Below: pink circle for where the sweatband meets the head and from there, fold up your chip:

Honestly, this works for so many kinds of hats. You can literally trace potato chips to make all of this easier until you become more familiar with the shapes (or just for fun):