I have a portrait of a boy from about 1920 in a sailor suit. His eyes are looking to the right, slightly and no smile. I am just wondering if you can paint the eyes looking into the "camera", give him a little smile and paint him in a white dress shirt.

We can probably do that.

Yes, things and subjects from multiple photos can be merged together into one painting if the orientations are conducive to doing so. To see examples of this being done you can check out our gallery at https://www.instapainting.com/gallery/merge-photos

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