Fashion engineer

Soon(tm) my employer might be having more of a dress code than I have now. This is acting as a motivation to start drinking and making my own clothing. I need non-athletic shoes and black/blue slacks. Fallback of course is I just buy stuff, but, if I have to rock a wardrobe that has specs that aren’t my favorite, why not do it awesome.
Shoes. I wear skate sites primarily. They usually have a good sole, and arch support and a mellow style. Done in leather and they’re almost stealthed. By the way, my phone didn’t know the word stealthed; fixed. Now every time I kill another pair of shoes, I keep them. Shoes have been on my radar for a while now. I want a thicker sole. I want an interchangeable sole. And I want sites that don’t break out at the same place every pair of shoes I’ve ever had do. I’ll probably saw apart a pair later this week to see what I can see on the internals. That and start sourcing materials.
Trousers are both easier and harder. I have a pair that fits me fine, but they tore out. So first, seam rip those bad boys. Let’s get an idea of what I’m doing. Then, much like the shoes, all my clothes fail in the same way every time. I need to look for ways to mange them not fail there. Ankle slits and tapered hens should take care of half the problem. The crotch is a bit more difficult.