[LI SNOWBIRD]

This is kind specific association game.
The object is to name people that (you think) wear a "funny hat" and get away with it.
I'll start: Carmen Miranda and Napoleon

[DougB]

Abe Lincoln and Hoss Cartwright

[Chi-Town]

Ralph and Ed when they attended Royal Order of Raccoons meetings

[redwitch]

Fred Flintstone at his lodge meetings.

[2newyorkers]

All the women in My Fair Lady especially at the horse race.

[mac9]

Pharrell Williams

[NYGUY]

The Queen of England

[Villager Joyce]

I didn't read tbe question carefully so my answer needed to be erased. Sorry.

[BobandMary]

Princesses Beatrice and Eugenie at the Royal Wedding. Beautiful young women.... but the hats scared me.

[LI SNOWBIRD]

Haha all great-
I'll add more-- Santa Claus and Archbishops MitrHaha

[redwitch]

Smokey the Bear hats worn by anyone but Smokey the Bear and drill sergeants (they can wear whatever headgear they like -- I ain't gonna laugh). Hard to take a State Trooper seriously when his hat goes flying in the wind as he's lecturing you.

Madame Pompadour with her itty bitty hats on top of her great big wigs.

The kid from Our Gang (Spanky?) who had the beanie with the prop on top. Ditto George Jetson's son.

[CarolSells]

Minnie Pearl
Miss Gulch ( the lady in TWOO who takes TOTO from Dorothy)
The Tin Man
Clem Kadiddlehopper