Upload & Sell: On
The uncropped headshot is much better than your cropped/framed version. I find the cropping a little tight, but am not bothered by the glasses.
I would agree that it's important to master "inside the box," but putting a distressing crop in an ugly digital frame and text that looks like a watermark is not exactly thinking "outside the box." A similar headshot to your uncropped version, but a little looser would be a very agreeable image.