The other day, I almost dropped one of our last remaining drinkware glasses from our honeymoon. I was putting it into the cabinet, and it slipped; somehow, I caught it midair with ninja-like reflexes.
We used to have two glasses. We accidentally broke the other one years ago.
This one (the one that almost slammed onto the countertop) feels extra special now. Not because it’s fancy or valuable, but because of what it reminds me of our honeymoon, early marriage, laughter over drinks, and a slower season.
It’s easy to get attached to items that carry memories. I get it.
That near-drop made me remember something: even if that glass had shattered into a million pieces, the memory would still be there.
That glass isn’t the memory. It’s just a reminder of it.

That truth hit again last week when I cleaned out my daughters’ old dress-up costumes.
Ohhh, the memories wrapped up in those silly little outfits. They would be Captain Hook, making their entire stuffie collection “walk the plank”, swords in hand… wild giggles and fully acted out stories. I wanted to keep them all.
The thing is, though, they doesn’t play with them anymore. (However, if you have a themed dress-up party, they will have the best, most thought-out costume there!)
But I remembered: I have the memories. I have the photos. They still have their beautiful imaginations. Now, another little girl out there can use those costumes to spark her imagination and have wildly imaginative stories to act out.
Letting go isn’t letting go of the love. It’s making space for what matters now.
Why Sentimental Clutter Is So Hard
When something reminds us of a meaningful moment or a person we love, it feels wrong to let it go. We worry we’ll forget. Or that letting go means we didn’t care.
Sometimes we even hold onto things for someone else—a future child, a family member, or just because we feel guilty tossing it out.
But the truth is: memories live in us, not in our stuff.
You Don’t Need the Item to Keep the Memory
There are so many ways to hold onto a memory without keeping the physical item:
- Take a photo of it
- Write down the story behind it
- Start a small, intentional memory box
- Share the memory with someone else
The emotional connection doesn’t vanish just because the item does.
How to Let Go of Sentimental Clutter (Without the Guilt)
Here are a few steps to help when the item feels “too special to toss”:
- Ask yourself: Does this still serve a purpose or bring me joy?
- Take a photo before letting go
- Write down the memory or journal about why it was special
- Keep just one item from a group (like one favorite baby outfit instead of ten)
- Create a memory box with intention—not as a catch-all bin
What to Keep
- Truly irreplaceable items (like handwritten notes or heirlooms)
- Things you actively use or display
- Items that spark real joy or conversation
What to Let Go
- Things that have been hidden in boxes for years
- Duplicates or excess (you probably don’t need every baby blanket)
- Things from a season of life you’re no longer in
A Few Gentle Tips
- Do it in small chunks. Don’t tackle everything at once.
- Talk through memories as you declutter. It helps.
- Let your future peace guide your decisions, not guilt.

Let Go of Sentimental Clutter Without the Guilt
You can honor your memories without keeping every item.
The glass from our honeymoon still sits in our cabinet—and yes, I drink from it with more appreciation now. The costumes? They’ve gone on to a new home, and I smile when I think about the next little girl playing in them.
Letting go isn’t about forgetting. It’s about freeing up space to live now.
If you’re working through sentimental clutter, these posts can help:
- Life-Changing Magic? The Harsh Reality of Why Decluttering is So Hard
- 11 Simple Decluttering Questions You Should be Asking to Maximize Results
You’ve got this. Progress over perfection, always. ❤️
Selling My Clutter for Cash (And Teaching My Kids How To Do It Too)