His shirt had large elbow holes in the pocket, so when I was in the garment district, I picked up brown suede elbow patches by Dritz (available online if your local notion store doesn't have them). Fella teaches college classes, so the old school elbow patches are a nice touch.
If I had to do it again, I think I would have used iron on patches first on the shirt to make the sleeve more solid, but this works fine for now.



The hard part is lining up the patches so they're relative even. I did this by covering up the bigger whole (the right one) the best I could and pinning it. (Three pins, and I ruined 2 other pins trying to pierce the leather/suede). Then I sewed through the holes twice (just a regular stitch, with resulted in something like this the first time around:)
The second time around, I sewed through the opposite holes, making the stitching complete around the holes.

Fella was pleased with these results. It took me about 1 hour and some change (I watched a few episodes of UK Office, which are now streaming on Hulu, after dinner). But I informed him that since I mended the shirt, we have to share it. He was just relieved that I did not commandeer it entirely.

Edit: I also tried it with a belt. I like this look a lot too, but I think a longer, looser belt wore a bit lower would look best. (At the natural waist looked a bit odd with all the loose fabric).