I find it interesting that “Wear a Hat” day falls on the same days as “Good Hair” Day. It is as if we cannot make up our minds on what kind of days is March 26th – a day that requires a hat or not. Personally, if I was judging it off the weather outside today, it would be a hat day. I prefer to rock a Blue Chair Bay Rum trucker’s hat.

But this got me to thinking about characters who also had a great hat game or just popular hats mentioned in some of my favorite novels or series and here is my top 10 list.

10. Waldo’s hat from Where’s Waldo

How many hours have society spent looking for the boy wearing that hat? A sock cap is not my favorite type of hat. I find them often to be too hot.

9. The Mad Hatter from Alice in Wonderland

I found the Mad Hatter to be a terrifying character in Alice in Wonderland. Actually, I found the who story line truly terrifying. Alice getting lost in this crazy world with little to no rules was just not for me.

8. Holden Caulfield in The Catcher in the Rye

Holden’s red hunting cap was just another way that the character isolated himself from the society and the world around him.

7. Jay Gatsby in The Great Gatsby

Jay is described as wearing a flat cap when he and Nick take a drive and he shows him his war medals. Many haberdasheries advertise the flat cap as a “Gatsby”.

6. Jeeves in My Man Jeeves

Jeeves is a godlike man in a bowler hat with grave, finely chiselled features and a head that stuck out at the back, indicating great brain power.

5. Dolly Varden in Barnaby Rudge

This Charles Dickens’ character was known to fashionably dress with inspired the Dolly Varden costume, which was typically a hat with large flower and lace trimming and an equally fashionable dress.

4. Santa’s hat in multiple works

The Santa’s Hat is not a modern invention. It can be tied back to both the early church and sun worship by pagans.

3. The Cat in The Cat and the Hat

The tall, red and white striped hat has been associated with the mischievous cat who causes trouble for a young boy and girl who are bored on a rainy day.

2. The Sorting Hat from the Harry Potter series

The Sorting Hat was worn by every young witch and wizard to pass through Hogwarts School. It sorted the pupils into the respected houses based on character traits.

1. Sherlock Holmes in multiple works

The deerstalker hat has been associated with Sherlock Holmes, but Holmes is never described as wearing a hat in any of the literature. The association comes from an illustration in one of the volumes.

Which characters do you associate with hats?