It's a funny thing about hats. Some people can "do" hats--some most definitely cannot. The beret that looks jaunty and artistic on one may have a mushroom-head effect on another. The straw hat that looks so breezy on carefree on one person...well, you get the point. However, baked goods made to look like (or inspired by) hats seem to work a little bit more universally. Now, we could really go wild on this theme--from Pilgrims' Hats to Southern Belles to Nuns Habits, a lot of hat-pastry connections have been made over the years. But for now, let's just focus on two, with respective histories as rich as their sweet buttery cookie crusts:

Hamentashen: These tricorner cookies are folded over on the top so as to reveal just a small, alluring bit of the filling within, usually poppyseed, apricot or prune. Don't let those flavors put you off: really, they're very good, almost like a danish but with a cookie crust. As for the hat that inspired it all? According to Wikipedia, the name hamantash (המן־טאַש), is a reference to Haman, the villain of Purim, as described in the Book of Esther. Apparently,

a likely source of the name is a corruption of the Yiddish word מאן־טאשן (montashn) or the German word mohntaschen, both meaning poppyseed-filled pouches; over time, this name was transformed to hamantashen, likely by association with Haman. In Israel, they are called אוזני המן (Oznei Haman), Hebrew for "Haman's ears" where children are taught these tasty pastries are the ears of Haman that fell off at his execution.

However, ears aren't necessarily the most appetizing cookie inspiration, which is probably why

some Hebrew schools teach that Hamentashen are made in the shape of Haman's hat. There's even a song to go along with it (sung to the tune of "Carnival of Venice"):

My hat it has three corners.
Three corners has my hat.
And had it not three corners,
It wouldn't be my hat.

Napoleonhattar (Napoleon's Hat): We first came across this cookie at local Swedish bakery Larsen's; while we can't say why the Swedes saw fit to name a cookie after the petite ruler's signature hat, we can guess that it dates back to their involvement in the Napoleonic Wars. More important than the roots though, is the joy that this cookie has brought to our lives. Larsen's version was fully covered on top, with an outer cookie crust and almond paste-innards that approached the chewy consistency that one might expect in the center of a coconut macaroon. As an added bonus, theirs was chocolate-dipped on the bottom for extra decadence. We located a recipe in the Sunset Magazine archives, but theirs more closely resembles Hamentashen (at least visually).

Recipe Links:

Hamentashen: You can find recipes at jewishappleseed.org or this one looks good too!

Napoleon's Hats: Does anyone have a good recipe for them? We could only find a few; you could try the one we found in Sunset Magazine, or you could try this one. We couldn't find a recipe for chocolate-dipped ones, but probably you could do it the same way you'd do chocolate-dipped coconut macaroons.