So I found some redwing postmans for less than $40, but they're slightly wrinkled like pic related. Is it worth it to buy them?
I rescind what I said earlier. $40 for postmans in decent condition is a great deal, and they'll probably last you a good while.
That said, I hate how chunky they and other red wing shoes look in general. If you want a good looking derby that won't fall apart on you a few months in, you will need to shell out $$$, like $300+, unless you find a great deal on some used shoes.
Examples of brands you might want to keep eyes on are meermin, carmina, viberg, and alden. There are plenty of other brands I can't name off the top of my head right now.