Consider the Bang & Olufsen H6. B&O recently discontinued all of its wired headphones, including the H6, and you may find attractive pricing. The current B&H price is $300, which is certainly less than I paid when I purchased the H6 (gen. 1), but the price may come down. Might be worth calling a B&O shop directly to see if they have a set in stock and, if so, what they want for it.
I own five pair of headphones ranging in price from US$130 to $600, and the H6s are for me the most comfortable. There’s no problem driving them from an iPhone (if I recall, impedence is 31 Ohms), and I like the sound a lot for both classical and jazz. Some people think that the H6 (gen. 2), which is what you would get if you purchased new, has a bit more bass emphasis than my gen. 1.
I should mention that replacement earpads are not cheap ($57 the pair), but if I recall they are made of lamb skin or similar, which would explain that.