The Italian painter Tomaso Barisini da Modena (1325-1379) was one of the first to depict a person wearing a spectacle. The above painting dates back to 1352.
There has been a bit of debate on the first painting to have a person wearing spectacle as discussed in the below reference. The history of spectacles itself is interesting, and their origins is also hotly debated among historians of science.
To give you a flavor of the debate, let me quote E. Rosen, “The Invention of Eyeglasses,” Journal of the History of Medicine and Allied Sciences 1 1 (1956), p.13. :
“Much has been written, ranging from the valuable to the worthless, about the invention of eyeglasses; but when it is all summed up, the fact remains that the world has found lenses on its nose without knowing whom to thank.”
Similarly, the origins of telescope are also under debate [1]:
“if victory has a thousand fathers, as it is commonly said, then the invention of spectacles and of its derivative, the telescope (another nominee listed among the top inventions of the last two millennia), must have just as many.”
[1] Ilardi, Vincent. 2007. Renaissance Vision from Spectacles to Telescopes. Philadelphia, PA : American Philosophical Society. http://archive.org/details/bub_gb_peIL7hVQUmwC.
VISMAYA - History & Philosophy of Physics 