"Welcome" to SF. I'm going to make a few judgements that may or may not be true. You probably think $300 is a ridiculous amount of money to pay for shoes, and you probably think the second pair of shoes you posted look reasonable (you said you didn't like the first, but you liked the fabric of the second). I'm not trying to insult you, because I was there once. So were most people here. If you spend enough time here, however, you will eventually develop a gag reflex when you see shoes like the ones you posted. $300 for a pair of shoes will also become customary, because you will understand and appreciate why they are $300. In the meantime, though, here is my advice for you:
If you are in the sub $100 range, try to learn about classic shoe designs and then buy a pair of shoes that are classic in design, but perhaps not of the finest materials and construction. I don't have many suggestions for you, but from what I've seen, some Bostonians are reasonable, such as
these. Spend some time on the
Allen Edmonds (AE) website for educational purposes, to familiarize yourself with the various classic shoe styles. I mention AE because they are considered the standard, entry-level quality shoe manufacturer around here, and most of their shoes are very classic.
When you are in the position to invest in a pair of nice shoes, you will be ahead of the game if you have already developed an eye for quality. Or turn away now and save yourself and your wallet.

Good luck.