So true. I'm still kicking myself for passing on this Paul Smith jacket back in 2012.
You should look into getting yourself some leather shoes like a pair of oxfords or derbys, just in case you need to look a little more formal for certain events. Plus, if by "pants" you mean traditional trousers (and not jeans), then sneakers are going to look weird, most likely.
Unfortunately, when it comes to leather shoes, I can't really think of anything that wouldn't suck up your entire price range. And if possible, you should really make the investment into something good. Footwear (particularly leather footwear), is probably the best investment you can make in fashion, considering how long it'll last you (good stuff anyway), and the fact that you won't ever grow out of your shoe size. Maybe it's not something you spring for right now, but definitely something to look for in the future, if you've got some extra budget.
Yeah, I'm not wearing jeans. I've been hunting around thrift stores for shirts, but pants and shoes are more specific in dimensions that even if I find a nice pair, chances are they don't fit.
The Tigers are super comfortable and professional looking, given them being black and gray, and don't clash with the pants I do have (at least, I don't think so). The pants are cotton with some elastine. Basic nicer pants from H&M - sorry, don't know the term for them, haha.
So, no budget shoe options in the styles you mentioned? I could just put some inserts for arch support, etc.
There are some ~$100 Oxfords at Nordstrom. I feel that is within my budget, based on other things I get, just for reference. past $150 will be too much, I fear.
EDIT:
Also in the market for a means to carry materials (Surface, notebooks, planner, pens, etc.). Side bag or something similar.