My grandma always wore hats! She did wear pant suits though :) She was a traveling sales rep and she always dressed for work! She was known as the hat lady. For several years she only had a couple of hats. People were always commenting on the huge variety of hats that she had :) She then would tell them that it was the same 3 hats. She just had a ton of silk ribbons that she always tied on them! Then as the years went by she had quite the collection.
When she passed away, all of her daughters and daughter in-laws, and all of us granddaughters all wore one of her hats to the funeral. It made us all feel like we had a little bit of her with us.