I make fine-art portrait books from family photos for a living — over 4,000 of them so far, and I still review every portrait by hand before anything prints. Which means I’ve now looked at more family photos than almost anyone alive, and I can tell you the surprising truth about what photo works best for a custom portrait.
It’s not the sharpest photo. It’s not the newest phone. The best photo is the one you already love. If a picture makes you feel the person — that particular smile, the expression you’d know anywhere — it will make a portrait that feels like them. If a technically perfect photo leaves you cold, the portrait will too. You are the world’s leading expert on this face; trust that.
Everything below is just detail on top of that one rule. This guide is for portraits of anyone, by the way — grandchildren, grown children, parents, grandparents — and it applies whether you’re making the fourteen-portrait book or simply trying the free three-portrait preview. The word “child” below means “the person in your book,” at any age.
The photo
Van Gogh
Klimt
Rockwell
At a glance: which photos work
| The photo | Verdict | Show-off factor in the portrait |
|---|---|---|
| A photo you already love | Works beautifully | ★★★★★ |
| Facing the camera, both eyes visible | Works beautifully | ★★★★★ |
| Shoulders up, face clear | Works beautifully | ★★★★★ |
| Several photos, different expressions | Works beautifully | ★★★★★ |
| A calm, everyday expression (the anchor) | Works beautifully | ★★★★★ |
| Everyday eyeglasses | Works beautifully | ★★★★☆ |
| A full-length standing shot | Workable — I crop in | ★★★★☆ |
| Braces or missing teeth (send two) | Workable — send a backup | ★★★★☆ |
| The silly one, tongue out (pair with a calm one) | Workable — send a backup | ★★★★☆ |
| A hat (add one bare-headed photo) | Workable — send a backup | ★★★☆☆ |
| A group shot (tell me who) | Workable — send a backup | ★★★☆☆ |
| A full profile / side angle | Workable — send a backup | ★★★☆☆ |
| Sunglasses | Please avoid | ★☆☆☆☆ |
| Face paint | Please avoid | ★☆☆☆☆ |
| A screenshot of a screenshot | Please avoid | ★☆☆☆☆ |
1. Start with a photo you love
Scroll your camera roll and stop at the one that makes you smile. That reaction is data: it means the expression is theirs — the one you recognize, the one you’d want on the wall in fifty years. This is the single best predictor of a portrait you’ll love, and it beats every technical rule on this list.
One note here, because it comes up often: sometimes the photo a grandparent loves most is the silly one — tongue sticking out, mid-giggle. Send it! A silly portrait is wonderful once or twice in a book. But pair it with a photo of their calm, everyday face — the expression that’s simply them. That neutral photo is the anchor: it’s the reference I use to keep the likeness true across every portrait, and it’s the face most of the book should carry.
Not sure the photo will work? The upload is the test.
See three portraits made from it in about a minute — free, no card, nothing to cancel.
See your free portraits →2. Facing the camera is best
A front-facing photo shows me both eyes, the shape of the smile, the proportions of the face — everything a portrait lives on. A three-quarter angle is fine too. A full profile is workable, but if you send one, add a second photo facing forward so I have the whole face to work from.
A word on light, since people ask: daylight from a window is ideal, but ordinary indoor light is fine — I can lift a slightly dark photo. What I can’t fix is a face lost in deep shadow or blown out by a flash, so if you have a choice, pick the photo where you can see both eyes clearly.
3. Shoulders up is the sweet spot — but any framing works
Head and shoulders, face nice and large in the frame: perfect. But don’t discard a full-length photo of someone standing — I crop in. What matters is that the face is in focus and not tiny.
4. Send several photos, with different expressions
One photo works. Three photos work better. Different expressions — grinning, calm, mid-laugh — show me what’s permanent in the face versus what belongs to one moment. That’s exactly what a painter sitting with a subject would study, and it’s the closest you can get to giving me a live sitting.
Whatever mix you send, make sure one of them is the neutral, everyday expression. Playful faces get painted once or twice; the everyday face is what the book is built on.
5. Braces or missing teeth? Send two photos
Nothing wrong with either — they’re part of the story of a face. But send one photo with a closed-mouth smile and one with the full grin, and tell me which way you’d like the portraits to go. (Grandparents are split about 50/50 on this; there’s no wrong answer.)
6. Hats are fine — with a backup
A beloved cap or a sun hat is okay. But hats hide the hairline and change the shape of the head, so add at least one bare-headed photo alongside it.
7. Sunglasses — please, no
The eyes carry more of a likeness than every other feature combined. A photo in sunglasses asks me to invent the most important part of the face, and I won’t guess at that. Regular eyeglasses are completely fine — if they’re part of how the person looks, they belong in the portrait.
8. Face paint: usually not workable
The butterfly-cheek festival photo is adorable, but paint covers the very skin tones and contours a portrait is built from. Save it for the family album and send me the photo from before the face-painting booth.
9. Group photos: workable, not ideal
If the best expression you have lives inside a group shot, send it — just tell me clearly which person the book is for. A solo photo is still better: faces in group shots tend to be smaller and softer. If you can, send the group photo plus any solo shot, even an imperfect one.
10. About resolution: helpful, but not everything
A crisp original beats a blurry one, so send the photo itself rather than a screenshot of a screenshot, and skip heavy filters if you can. But don’t let resolution stop you — I’ve made beautiful books from decade-old photos and ordinary phone snapshots. Expression beats pixels, every time.
One request, not about quality: please don’t upload photos of babies or toddlers with their shirt off. Even when the photo is completely innocent — bath time, the beach — I’d simply rather those photos not be sent to me. A dressed photo from the same day works perfectly.
Clear face, natural light — perfect
Group shot — workable, tell me who
Too far away — the face is tiny
Face blocked or dark — send another
How to choose in 60 seconds
- You have hundreds of photos: pick the three you’d save in a fire. Different expressions if possible. Done.
- You only have a few: send what you have. Group shots, hats, standing shots — I can work with far more than you’d think, and I’ll tell you honestly if I can’t.
- You’re between two photos: send both. More is always better than fewer.
- You’re still unsure: upload one and look at the free preview. The preview is the answer to “will this photo work?” — you’ll see it with your own eyes in about a minute.
And if you’re stuck, reply to any of my emails with the photos you’re considering. I answer every email myself, and I’d rather spend two minutes advising you than have you stall for a month on photo doubt.
Pick the photo you love. See it as fine art in about a minute.
Three portraits from your photo, free. If they don’t look like them, you’ve lost a minute — and learned which photo to try next.
Try the free preview →What happens after you choose
Once you’ve picked the photo, my part starts. I choose the other eleven painters to suit that one face, review every portrait by hand, and nothing prints until you’ve approved every page. If a portrait doesn’t look like them, I redo it — or refund you. I wrote up every receipt of how the process works for people who want to check before they trust me with a photo.
If you’re choosing the photo for a gift, two of my other guides may help: gifts a grandmother will actually show off, and legacy gifts for grandchildren — the ones that survive a decade.
Frequently asked questions
Does photo resolution matter for a custom portrait?
It helps, but it’s not the deciding factor. Send the original file rather than a compressed screenshot, and avoid heavy filters. A slightly soft photo with a beloved expression beats a razor-sharp photo with a stiff one.
Can I use a photo with other people in it?
Yes — just tell me clearly who the portrait is for. Solo photos are better because the face is larger, so if you have both, send both.
What if they have braces or missing front teeth?
Send two photos — one closed-mouth, one full grin — and tell me which you’d prefer in the portraits. Both make lovely books.
Do you make portraits of adults and grandparents, or just children?
Anyone. The books began with grandchildren, but I make them for grown children, parents, grandparents — any face someone loves.
Can they wear a hat or glasses in the photo?
Everyday glasses, yes — they’re part of the face. Hats are fine if you add one bare-headed photo. Sunglasses, no: I can’t invent the eyes.
How many photos should I upload?
One is enough to start. Two or three with different expressions is ideal. There’s no prize for restraint — more photos only help.
The short version
The photo you already love is the right photo. Face the camera, shoulders up, no sunglasses, extras welcome. Everything else, I handle — every portrait is reviewed by hand, nothing prints until you approve it, and if you don’t love it, I redo it or refund you.
The one you’d save in a fire
That’s the photo. See it painted by the masters in about a minute — free.
Start with your photo →
David Woodworth
Founder & Art Director, Wyrd Story
I founded Wyrd Story to make museum-grade keepsakes of the people we love — over 4,000 books so far. I review every portrait by hand before anything prints, and I answer every email myself.
