14 Things Experts Say You’ll Regret Tossing

When you start decluttering your space, it’s easy to focus on what to get rid of. But not everything you toss today will feel like the right choice down the road. Knowing which items are worth holding onto can save you from future regret.

Organization specialists highlight certain belongings that tend to hold unexpected value over time, even if they don’t seem important at first. This guide will help you recognize the things you’ll wish you kept, making your organizing efforts smarter and less stressful.

Family photo albums

Old photo albums, black and white vintage photographs, family memories preserved, historical portraits and scenes
Image Credit: Thiago José Amaral/Pexels.

You might feel ready to get rid of old photo albums, but they hold more value than you think. These albums capture memories you can’t replace and can connect you to your family’s history.

If space is tight, consider digitizing the photos before letting go of the physical copies. This way, you keep the memories safe and easy to access.

Also, check if local historical groups or online communities would appreciate the albums. They can help preserve your family’s legacy in a meaningful way.

Handwritten letters from loved ones

Stack of vintage letters and photographs tied with string on a rustic wooden table
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You might feel unsure about keeping old letters, but they hold a unique personal touch. Handwritten notes capture emotions and moments you can’t replicate with digital messages.

Even if the words seem simple, the handwriting itself connects you to the person who wrote them. Tossing these letters might lead to regret later when you wish you had that tangible memory.

Holding onto a few meaningful letters can bring comfort and keep your loved one’s presence close, especially during hard times.

Favorite childhood toys

Close-up of colorful toy race cars arranged in rows on a wooden surface, featuring various models and designs
Image Credit: Shutterstock.

You might think tossing old toys is no big deal, but you could regret it later. These items often carry strong memories and a sense of comfort.

Keeping one or two favorites on display can be a simple way to hold onto those moments.

If space is tight, taking photos before letting toys go helps keep the memories alive without the clutter.

Your childhood toys aren’t just things—they’re links to your past that may feel valuable someday.

Unique handmade gifts

Two neatly wrapped gifts in brown paper, tied with twine bows, decorated with small green flower bundles, heart-shaped tags, and mini clothespins, resting on a lace-patterned white cloth
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You might be tempted to toss old handmade gifts when decluttering. But these items often carry personal stories that you won’t want to forget.

Handmade gifts are unique and can’t easily be replaced. Holding onto them helps preserve memories and connections with the giver.

Even small handmade items can add character to your space. Keeping them can remind you of special moments and thoughtful gestures.

Heirloom jewelry pieces

Hands holding assorted jewelry, pearl necklaces, gold and gemstone accessories, open jewelry box, vintage ornaments, elegant and intricate designs, delicate craftsmanship, personal valuables
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You might feel tempted to toss heirloom jewelry because it seems outdated or bulky. However, these pieces often carry family history and special meaning that can’t be replaced.

Even if you don’t wear them, keeping heirloom jewelry can connect you to your past. It can also become a meaningful gift for future generations.

If you decide not to keep certain pieces, consider talking with family members first. Someone else may want to cherish those items or remember the stories behind them.

Travel souvenirs with stories

Market stall with assorted traditional silverware, ornate trays, religious icons, ceramic plates, glassware, and decorative souvenirs, vibrant and detailed display
Image Credit: Zorro2212 With Barbara Z.- CC BY-SA 3.0/Wiki Commons.

You might feel tempted to toss some travel souvenirs, but those items often hold memories you can’t replace. A small magnet or a postcard can bring back the places you’ve been and the experiences you had.

These souvenirs carry stories only you know. Keeping them helps you relive moments and share them with others later.

Remember, the value isn’t in the object itself but what it reminds you of—your adventures, people met, and lessons learned.

Old recipe cards from relatives

a collection of vintage handwritten recipe cards, aged paper, faded ink, overlapping layout, nostalgic and rustic kitchen feel, some cards with stains and torn edges.
Image Credit: Esty

You might think old recipe cards are just clutter, but they hold more than instructions. These cards connect you to family moments and traditions that shaped your holidays and celebrations.

Keeping them preserves memories of loved ones who created those dishes. Plus, they often include personal notes or tweaks you won’t find in cookbooks.

When you discard these cards, you lose part of your family’s story. Holding on to them keeps that history alive and can inspire your own cooking.

Books with personalized inscriptions

Books with personalized inscriptions
Image Credit: Esty

You might think a book is just paper and print, but an inscription makes it special. If a book has a handwritten note from someone important to you, it holds memories beyond the story.

These personal messages can remind you of moments, places, or people. Tossing them means losing that small, meaningful connection. Keep them to revisit those feelings whenever you want.

Original artwork by friends or family

Paintings in a Room
Image Credit: Kampus Production / Pexels

You might think about tossing original artwork from friends or family when decluttering. But these pieces often hold personal meaning that photos just can’t capture.

Keeping them can remind you of special moments and the creativity shared with loved ones. Even if the art isn’t perfect, it’s a connection to someone important in your life.

You don’t need to keep everything, but choosing a few meaningful pieces can brighten your space and your memories.

Wedding keepsakes

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You might be tempted to toss old wedding items, but many experts advise keeping certain keepsakes. Your wedding dress, invitations, and handwritten vows hold sentimental value you’ll appreciate later.

Photos and small mementos from the day are worth saving too. They remind you of the people and moments that made your day special. Don’t rush to declutter these; they often bring comfort and happy memories.

Personal journals or diaries

A Person Writing on a Diary
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You might regret tossing your personal journals or diaries. They capture your thoughts and feelings, showing how much you’ve grown over time.

Old entries can remind you of challenges you overcame. You may also find joy in revisiting moments you once documented.

Even if some pages feel embarrassing, they hold value in understanding your past self. Keeping them allows you to track your personal journey clearly.

Crafts made by children

two young girls painting Easter eggs, smiling, seated at a kitchen table, colorful eggs, candy bowl, sign reading “Happy Easter Day”
Image credit: Eren Li/Pexels.

You might feel like tossing your kids’ crafts when clutter builds up. But these pieces often hold special memories and show their creativity.

Keeping a few handmade items can remind you of moments you shared and your child’s growth.

These crafts don’t need to take up much space, so choose the ones that mean the most to you. It’s a small way to treasure your family’s story.

Vintage concert tickets

Scattered vintage concert tickets on a wooden surface, featuring bands like Aerosmith, Foreigner, Ted Nugent, Charlie Daniels Band, and Blue Öyster Cult, various dates and seat numbers visible, faded paper with colorful designs, nostalgic memorabilia from past events
Image Credit: Shutterstock.

You might feel like tossing old concert tickets, but they hold more than just paper. These tickets capture moments that mattered and can bring back great memories.

Even if the band wasn’t your favorite anymore, the tickets mark experiences you lived through. They also make for unique keepsakes that tell your personal story.

Saving them can add charm to your space or be a conversation starter with friends.

Special awards and certificates

Close-up of a person’s hand reaching for a small gold trophy, several other trophies in different shapes and colors arranged on a wooden shelf, framed photo partially visible, wallpapered background
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You might think old awards or certificates are just clutter, but they tell your story. These items remind you of achievements and milestones that shaped your journey.

Keeping them helps you reflect on your growth and stay motivated. Even if a job or activity didn’t last, the recognition still holds value. Holding on to these keeps a part of your personal history alive.