So, the floppy shoe situation – I thought I had it all figured out. Sam needed to run some errands last weekend, so we went to our favorite store: Harbor Freight. There, I purchased a grommet/eyelet tool and a bunch of perfect, shoelace-sized grommets. This was going to be so easy!

I decided to begin this project before church on Sunday. I took a deep breath and plunged the awl on Lloyd’s pocketknife into my quasi-new shoes. (The other shoe is there for measurement help.)

As it turns out, poking holes in shoes is incredibly easy. However, realizing that you don’t just need to poke holes but that you need to remove the actual material from the future grommet-sized hole (and that you can’t) causes one to break out into flop sweat, and one has already taken one’s shower before church.
Ugh. I just went to church all gross and figured it out later.
Later in the day I tried using a drill to enlarge the holes (I didn’t want to order a leather punch), but it actually didn’t matter – the grommets that came with the kit were too shallow to go through both the leather and the cloth lining. Great. Just great. My solution?

Just put the shoelaces in the holes. It’s working great, even though one is kind of off. The shoes don’t flop around anymore, and now I just have the regret of buying a grommet kit.
Need any holes in anything? I’m your guy.
I have a leather punch. For future reference. 😉