>>2225934I'll do both, no worries.
>>2226097In the interests of not criticizing without being constructive, I'll explain why this looks sloppy and how doing it correctly isn't much more difficult than how you did it.
This is done with less than 10 layers in GIMP with a mouse, but you could do it with 3. I was just being "lazy" and GIMP isn't part of my normal workflow.
1st: Rectangle select to fill the white BG and outline, then the outline's ghost. Use a smooth brush to blend the 1-pixel transition.
2nd: Three-node path on new layer to trace the hair strand, path to selection, fill with black. Add a rectangle selection of the outer edges and clone stamp the checkerboard background fill up to the edge of the hair (on the original layer). Clone stamp lines from lens to cover corner of text box which is below hair strand.
Note: At this point you can fudge the rest and it will look clean, because there's no artifacts in the pure white BG and the silhouette hasn't been butchered. Always prioritize silhouette and background / white space first.
3rd: Three-node path on a new layer right above original for the glasses frame and highlight. Fill with checkerboard from face below eye. Trace outline with black.
4th: Selecting as needed from paths or rectangles, paint white outline of hair, white outline of glasses frame, shading just below hair strand, fix whatever's still wonky.
It took me about as long to write this as it did to modify the image, for what it's worth. Quick doesn't have to mean shitty and slow doesn't always mean good, but doing things correctly is always going to be more satisfying in the end.