How to Clear Sentimental Clutter (Without Feeling Guilty)

Two years ago, I said goodbye to my wedding dress. This might shock you, but I still don’t miss that dress at all!

I've never been super hesitant about decluttering sentimental items so I rarely keep things just because.

But please don't think I'm completely heartless.

I still have one small tote of memories from my childhood AND multiple shoeboxes stuffed with letters Joseph and I wrote to one another while we were dating.

(Although future me envisions a project where I scan those letters into the computer to create a print-and-ship keepsake album like the ones at Artifact Uprising. Then I could toss the original letters and save even more space!)

But that's ME.

I’m probably the exception…a crazy gal who now has you worried that her ruthless decluttering mindset will rub off on you.

Because for most people, saying goodbye and decluttering sentimental items is downright painful.

Some items trigger long-forgotten memories as they whisk you away to a specific time and place. When you so much as think about transferring those heavy boxes from your trunk to the musty-smelling local Goodwill drop-off spot, your equally heavy heart might feel like you are losing that memory forever.

Maybe you're not ready to give up your wedding dress. Or throw away your kid's artwork. Or sort through the box of knick-knacks left behind from grandma's house.

But what small step can you take?

Here are three things to consider:

1. Freedom comes from owning what you use and love, not what you’re emotionally hijacked into keeping. When you worry about giving away something you *might* need in the future or feel like a memory only lasts as long as you own the accompanying item, your stuff becomes your security…and later on, a burden. Not just to you. Others will need to make decisions about your stuff after you. Which leads me to my next point…
   
   
2. Not everyone will genuinely care about the things we leave behind. This is a hard truth to hear! (A mother may hope her daughter will wear her wedding dress, but she might want to choose her own dress. So why not donate it now so another bride can treasure this gem on her special day before it's yellowed and considered out-of-style?) Nothing is worth anything if no one wants it.
   
   
3. Holding onto too much stuff will guarantee unnecessary stress. People much smarter than I am have proved this! More things require more decisions. Like how to store and organize these items. And if you display them around your home, then you're trying to clean around them to make sure they don't clutter up the areas and tools you use every day.

My Favorite Decluttering Hack

If you're still feeling pretty overwhelmed (and emotional!) at the thought of sorting through and decluttering sentimental items, remember…you don't need to donate everything tomorrow!

Try this doable hack:

Put a bin in your closet where you can toss items you don’t use as you come across them. Then count how many times you think about what’s in that box. Or how many times you pull something out to use in the weeks/months that follow. 

99% of the time, you will never miss what you’ve stored away! But giving yourself this extra time will help you feel more confident about saying goodbye to everything inside.

However, if you're ready to take the plunge and open up long-lost boxes stuffed in your attic or basement, here's a quick roadmap you can follow.

Decluttering Sentimental Items Easily

First, get a feel for how much that item means to you.

• What or who does it remind you of?
• Are you currently using the item regularly?
• Does this item best represent a memory or is there a different one that offers more meaning?

Then decide whether to keep or declutter the item.

I like to do this in 2-3 rounds, tackling one box or one corner of a close at a time so I'm not overwhelmed!

The first round, go through the things that require easy decisions. Things you don't really have to think long and hard about. Then take a break and come back when you're mentally ready to sort more purposefully during round two.

This is what I did when I sorted through my large book collection. In the end, I donated seven boxes of books to the thrift store, but that was a month and three rounds of sorting later. Each time I sat down to comb through the books with renewed vigor and a better understanding of what I wanted to keep and why.

What Should You Do With the Items You Keep?

If you keep an item, think about how you could use, display, or repurpose it.

Could you incorporate a few plates from a treasured dish collection on a wall? Turn t-shirts into an old quilt? Scan kid's artwork into the computer and create a digital photo album?

If there's nowhere to put the item other than a box, give yourself one small keepsake box that you can fill without judgment. Both Joseph and I have one and what we keep is not allowed to spill over into another box.

This either/or helps me decide what's truly important to me and what's not. I would much rather keep my baby book than a high school volleyball trophy!

What Should You Do With the Items that Go?

There are a few options:

• Take a picture to put in a scrapbook where you can write down what that item meant to you and the memory that surfaces when you see it.

• Ask family members if they want the item, but a gentle warning here—prepare your heart for any “no's.” You don't want relatives to keep things because they feel like they have to, and then later take the steps you're taking right now.

• Donate the item to a local charity or thrift shop. But only if it's in good, usable condition! Use these donation guidelines if you're not sure. (And if you're wondering about having a yard sale, here's why I don't recommend that strategy.)

• Sell the item to an antique dealer. Check eBay to see what the item is selling for and call around to local antique shops and ask what they could offer you. But remember that they require a profit margin too, so don't expect the highest possible price for your item unless you are selling to a collector.

Regardless of what you choose to do with your things, you are not dishonoring the person or memory associated with them! No one can take those memories away from you.

Most of all, be kind to yourself during this process, because decluttering sentimental items is a process. You will learn to make quicker decisions the more you exercise your decluttering muscle.

But here's the best part.

Saving fewer items will give more meaning to the ones you do keep. Instead of multiple I-should-keep-this-but-I-don't-know-what-to-do-with-it “treasures” living in a box shoved into the darkest corner of your closet, you'll own a handful of real treasures that bring genuine joy.

Pin this post to reference later:

Disclosure: Some of the links in the post above are affiliate links. This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. Read my full disclosure policy here.