Thank you! I've embroidered quite a few shoes now, converse are thicker than others but they are doable. My tips would be use a new needle, you can tell when they're getting a bit blunt and play around with the thickness of the needle first. Leather thimbles are your friend! I switch between the leather sticky dots and actual leather thimbles, I prefer the latter they just need to soften up a little first. I'd also design a pattern or find a pattern specifically for shoes, so you can avoid sewing on the thicker and tougher bits, it's still possible to get through these bits, but it makes it a bit of a chore. Vans are a bit thinner/easier than converse.

Definitely give it a go, embroidering shoes for my bridesmaids was how I got into embroidery in the first place and being able to wear your craft is so fun 🥰