So, Vans just came out with a canvas high top line that is PERFECT for shoe painting. The reason I gave all my friends who were pushing me into doing custom shoes as a side business was that I couldn't find a suitable replacement for the discontinued shoes I originally used (I don't like Converse for several reasons
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I'd start by using both this pair and your roomie's test pair as a test case for how much time you spend. Pay close attention to how long it takes to do each piece, and if you think it'll speed up as you get more comfortable with it. Then you can calculate an hourly wage you consider worth your time and effort.
Then from the other side, you need to consider what you think your market will bear. Assuming the costs you stated above, if someone wants four characters and a stripe, you're already looking at $115 for the art, plus the cost of the shoes and shipping. You're hitting the $200 range fast. That's equivalent to a mid-to-high end collectible.
Wear and tear is, I think, going to be the primary concern of your customers. It certainly was my first question! Offering touch-ups for the cost of shipping will likely go a long way toward allaying those fears, though. And thus far it doesn't look like cracking or flaking is a problem.
Hypothetically, for myself I'd probably want to keep the cost below $200 or so. I think if I went any higher than that they'd start getting too "precious" and I'd be worried about leaving the house with them! So maybe the four characters/logos would be a good limit for me? The idea that popped into my head on the way to work was a character backed by a large logo, like Kaidan in front of a Spectre logo or something like that.
I would start by figuring out how long it takes you do to each element, then set a price structure based on that.
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I think the toughest thing for me right now is figuring out what people are willing to pay, because that's ultimately what will get me sales or not. All the stuff on my end is flexible, because I'm at a point where getting paid too little for my time is better than nothing at all. I'm definitely going to try to streamline my process with my friend's pair of shoes though. I actually managed to find non-Sharpie permanent pens to do the black outlines rather than having to painstakingly hand paint them on like my last pair (those were dark times).
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