Mildred’s 60 Hats

One of my favorite organizing stories is about Mildred. When I first met her, she did NOT want to leave her home for the retirement community her children had suggested. 

“I’m not ready.”

We talked a while. She showed me her home. We shared some food. Eventually, we made it to the back of her home, and out the window, I saw her garage. I asked her what was in it. She sized me up for a minute, but then with a sigh, she told me something she hadn’t told her kids:

“My hats are out there.”

We took a walk out to the garage. I didn’t see hats. But she explained they were in boxes, nearly 60 of them. We opened one, and a midnight blue cloche with velvet ribbon instantly recalled an earlier age. When she whispered, “This is why I can’t leave,” I got it. These were more than fashion choices. Each one told a story, captured a moment, reflected a feeling. They were her memories from each stage of her life stretching from the 1920s to her more recent past, carefully nested in tissue, preserved and treasured. 

But not enjoyed. 

“When was the last time you looked at them?” I asked. 

“Oh! I can’t even remember when,” she replied. 

I pulled out another. “That’s the one I got when my son was born,” she smiled. 

We took a few of the hats back inside her house and sat down at her kitchen table. I tested my hunch. “If we could find a way to bring these hats with you, would you be okay with moving?”


We talked through a few ideas. She didn’t like the idea of hanging them on the wall, but she did like the idea of photographing them and framing the photos together. 


“I can’t bear the thought of the hats going to a thrift store. I DON’T want somebody using them for Halloween!”

So, with Mildred’s blessing, I photographed those that still brought her joy (and there were some that didn’t!). And then I contacted the costume shop at a local theater who was delighted to have them. Mildred loved having the photographs in her new home. They were an easy way to relive good memories and start conversations with new people. 

And that’s the story of Mildred’s 60 Hats.

And of keeping what you most need from something, even as you let it go.

If you have something you can’t seem to part with or need some help going through things, I can help.  Contact me to find out more!

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