Originally Posted by jasonfoote303
I've tried doing this to a similar pair of brogues and was NOT happy with the results. The problem was all the perforations and jagged edges. I started by stripping all of the old polish with a product made to do that and then dyed them a darker brown. It was immediately apparent that the dye wasn't getting into the holes and you could see the lighter color showing through. I went back in with the solvent and q-tips and toothpicks but couldn't get it cleaned out enough to get the dye to penetrate.
A proper shoe repair shop may be able to do a satisfactory job but if you're an amateur like me, it's probably not worth risking.
If you do it again try a dauber brush. Not claiming to be a pro but it does take practice, doing a few coats of dye, and patience. Sometimes sending them to a pro (i.e., Ron Rider) would be worth it. If you consider how much you get paid hourly compared to the hours spent trying to dye shoes, Ron's fee would be significantly less.
Here is a quick example of what I did with before and after pics:
Good luck with it though!