The Art of Meaningful Gifting

There’s something about the holidays that makes even the most practical of us go a little soft around the edges. Maybe it’s the twinkle lights. Maybe it’s the glögg. Maybe it’s the fact that it’s pitch-black at 3:30 p.m. and our brains are confused. But every December, I catch myself thinking less about what to give and more about why.

Hand-drawn illustration of colorful holiday gift boxes, including a burgundy box with a green holly bow, a tall gold gift bag, and a navy gift wrapped in a yellow ribbon.

And honestly? The internet does not help. Everywhere you look it’s the same gift guides: candles, slippers, cozy socks, gadgets no one asked for. (I swear every kitchen has a mandolin that’s been used twice and is now silently judging from a drawer.) Or it’s the other extreme of so over the top gifts you start to question your sanity.

But meaningful gifting? That’s a whole different thing.

It’s not about the trend. It’s not about the price. It’s about connection — giving someone something that feels like them.

And that’s where illustration comes in (and I can help!)

Why Custom Art Hits Different

When someone opens a gift that was created just for them, there’s this immediate emotional spark. They know you “get” them.
A portrait of their home.
Their dog, looking exactly like the little gremlin-angel they adore.
A milestone moment that deserves to live somewhere other than a phone camera roll.
A favorite cocktail brought to life with personality.

Illustrated portrait of a stone home surrounded by lush gardens, leafy trees, and a winding stone path, drawn in Erin O’Leary’s signature Denim & Ink style.
Illustrated portrait of a fluffy dog named Leo holding a gingerbread cookie in its mouth, drawn in a warm, textured style.
Custom illustration of a woman sitting on a stack of labeled moving boxes while holding a set of house keys, wearing pinstripe trousers and a casual grey top.

It’s not just a gift — it’s a tiny time capsule.

I’ve illustrated homes families lived in for 40 years. Dogs who will always have a permanent place in someone’s heart. Navigating your first home purchase. These aren’t “just drawings.” They’re memories you can hold in your hands.

So What Makes a Gift Meaningful?

Here’s the secret (and it’s not rocket science): intention. You noticed something they love. You remembered a moment that mattered. You chose something personal instead of random.

That’s it. That’s the magic. It’s really that simple.

Whether it’s a framed illustration, a sweet handwritten note, or a print that captures a tiny piece of their world — it’s the thought and care that turn a gift into a keepsake.

When to Give Art

Honestly? Anytime there’s a story behind the moment.

New home → A house portrait to celebrate the fresh start.
Weddings & anniversaries → Something more personal than another registry item.
Birthdays & retirements → A nod to a favorite place or passion.
Corporate gifting → Art that actually feels human (not… branded merch with a logo the size of a dinner plate).

If there’s meaning behind it, art can tell it.

A Gift That Sticks Around

Trends come and go. Remember when EVERYONE wanted an veggie spiralizer for veggie noodles? Exactly. But art? Art stays. It gets framed, displayed, loved, and remembered long after the wrapping paper is gone.

And honestly, the world could use a little more thoughtful giving — and a lot less panic-buying.

Closing

If you want a gift this season that feels personal and thoughtful, the kind that actually makes someone smile (and maybe tear up a bit), I’d love to help bring it to life.

Homes, pets, cocktails, memories, moments. I illustrate the stories that matter.

Explore Custom Illustration Options

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A Very Swedish Christmas: Glöog, Tomtes, and Whole Lot of Herring