Shopping·10 min read

Sentimental Gifts That’ll Make Them Feel the Feels

our favorite sentimental holiday gifts
Photo: Brittany Sturrett | Credit: theSkimm
November 1, 2021

Holiday gift-giving can be packed with quite a few emotions. You’re trying to find the perfect thing to say ‘I love and appreciate you,’ something that feels unique to each person on your list. It’s not a small task and can be stressful, we feel ya.

To help you find that something special, we rounded up meaningful gifts for those closest to your heart. From adorable customized portraits to personalized jewelry, these thoughtful and sentimental things go above and beyond. We can promise you one thing: They will be treasured for years to come. (And may produce some happy tears.)

Want more holiday gifting ideas? Check out The Sleigh List — our guide to the perfect gifts for everyone on your A-list.

Custom pet portrait

A custom pet portrait to honor their most beloved family member...

As if their lives didn’t already revolve around their pets. Now their home decor can too. This lifelike portrait pays homage to their furry (or not-so-furry) friend, whether they own a dog, cat, horse, or reptile. The portrait can even come with a frame so it'll be ready to hang in their pet shrine. No shame. ($27.98+, PrintOurPet on Etsy)

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A digitized library of memories to ensure the family history lives on… 

Everyone has that pile of VHS tapes collecting dust in the back of their closets. Legacy Box will take them off your hands — along with a range of items from photos to reels to audio tapes — and digitize them onto a small thumb drive and DVD set. You even get an easy digital download sent to you. The service offers digitization of up to 40 items and sends the originals back along with the new versions. It’s never been easier to rewatch, revisit, and relive priceless family memories. ($65.98+, Legacybox)

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An adorable personalized family portrait

An adorable personalized family portrait that will bring out their animated side… 

Who wouldn’t love being turned into a cartoon? This designer creates custom illustrated family portraits featuring up to 15 people and pets. It’s a fun way to capture a wedding, a pair of newlyweds, a growing family, or just the cartoon lover in your life. Seriously, they’ve never looked this cute. ($60+, Discovering You on Etsy)

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A create-your-own reel viewer

A create-your-own reel viewer that’s like a walk down memory lane… 

Nostalgia is knocking. And now you and the fam can play with a fave childhood toy that’s filled with photos you’ve chosen yourself. One viewer comes with seven photos. For those who have a hard time narrowing down their most-wanted snaps, you can purchase additional reels, too. And for more amazing great gifts from Uncommon Goods, shop here. ($14.95+, Uncommon Goods)

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A fill-in-the-blank journal

A fill-in-the-blank journal that will make them feel so loved… 

If your partner’s (or family member’s) love language is words of affirmation, this fill-in-the-blank love journal will be a hit. It’s chock-full of writing prompts that’ll allow you to gush over what you love so much about them. It’s a keepsake they’ll surely hold on to and look back on for years to come. ($7.96, Amazon)

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A piece of jewelry in your handwriting

A piece of jewelry in your handwriting that’s a true sign of your bond… 

It doesn’t get much more personal than this. This shop takes your (or anyone’s) handwriting and reimagines it onto beautiful pieces of jewelry. Think: their name, a quote, even an inside joke on a necklace, bracelet, ring or pair of earrings. The designer also makes jewelry out of fingerprints, which you can browse here. So. Sweet. ($34.62, Amazon)

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A coordinate bracelet

A coordinate bracelet to commemorate a favorite place of theirs... ...

Maybe it’s their most-loved date spot, a proposal spot, or just a spot on the couch. This cuff bracelet (in gold, silver, or rose gold) lets them show off its coordinates to forever remember that special place. Think of it as a sweet and subtle nod to a happy memory that they’ll recall every time they look down. ($74+, Brook & York)

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A box of redeemable tickets

A box of redeemable tickets that’ll help them feel fully pampered...

A great way to say ‘I love you’ is to show them. This customizable ticket-to-love box comes with 10 redeemable tickets for things like a massage, their choice of movie, breakfast in bed, and more. Romance is in the air. ($40, Uncommon Goods)

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A watercolor portrait

A watercolor portrait that proves home is where the heart is… 

Whether they’re a new homeowner, or you wanna immortalize a childhood home of theirs, this customizable portrait is the sweetest (and coolest) way to do it. Your home of choice will instantly be turned into a piece of artwork. It comes in a range of sizes and is also available framed with a family name and address printed below. Genius. ($49.95+, Casa Bella Portraits on Etsy)

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A one-line-a-day journal

A one-line-a-day journal for the person who doesn’t have much time to journal…  

This handy notebook takes the big commitment out of the practice by prompting them to write a single line each day. The journal can hold up to five years’ of memories, making it easy for them to look back on a specific date and remember how they were feeling. It’s like a mini time capsule so they can see just how far they’ve come over the course of five years. ($15.26, Amazon)

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a collaborative journal

And a collaborative journal that celebrates the most unbreakable of bonds... 

Is there a person more sentimental than your mom during the holidays? Answer is probably not. This journal has prompts for both you and her to answer. You can pass the book back and forth, writing down shared memories, favorite traditions, and thoughts for the future. Don’t worry about Dad feeling left out — there’s one for him too. ($8.49, Amazon)

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A photo calendar

A photo calendar that’ll show them just how often you think of them…

Plan new memories and look back on existing ones all in one place. This calendar doubles as a schedule keeper and an art piece, customizable by design and number of photos each month. And they say print is dead. ($29+, Minted) 

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A photo puzzle

A photo puzzle that will make game night way more special...

No more landscapes or beach scenes. It’s time for a puzzle that’s got much more sentimental value. Just pick a photo and Shutterfly will turn it into a puzzle ranging from 60 pieces to over 1,000. If you’re looking back on a family vacay, you can even upload up to 17 photos for one masterpiece. Consider this the missing piece you’ve been looking for on your gift-giving list. ($32.98+, Shutterfly)

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A custom adventure map that’ll celebrate  your  travels together... 

A custom adventure map that’ll celebrate your travels together... 

For the travel buddy you love to explore with, this mountain map honors your favorite places and neatly ties five cities together to make one memorable art piece. Available framed or unframed and in multiple sizes, you can pick the cities of your most recent vacations, or choose the cities of big events (where you met, where you grew up together, etc.). Whatever the places are, highlighting them in this special way is sure to induce some awws and ooos. ($65+, A Gier Design on Etsy)

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A birthstone ornament

A birthstone ornament for the person who enjoys their birthday as much as the holiday season… 

The song goes “deck the halls with chic, personal ornaments,” right? These birthstone ones are a birthday and holiday gift all in one. Choose their birth month and they’ll receive a handmade, one-of-a-kind blown glass globe. A fun fact to tell them as they open their gift: It’s made with rock dust from the historic eruption of Mt. St. Helens. This one’s for the nature (or history) lovers in your life. ($25, Uncommon Goods)

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If you buy anything from this article, theSkimm may get something in return. Oh, and if something’s out of stock, oops, it was there (and all prices were accurate) when we published. Thanks.

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