The cheapest audiophile quality headphones I know of are Grado 60s (Photo right). They’re available from a few top-end retailers for under $100 and worth every penny.
Both the Fiio line and the Grado headphones of all types are available from Headphoneshop on Yonge Street south of the 401 and worth the visit. Just keep control of your wallet. I went in a couple of weeks ago to buy a DAC for around $75 (my secret high price was no more than $300) and I came back after a few trips with what I paid for my first car!
Of course with equipment this good you’ll want to get a subscription to Spotify for $10 a month which streams CD quality audio or Tidal at $20 a month which streams lossless files more than twice the size.
Regardless of which way you go, you will be treated to some of the best listening you’ve every heard. I’ve setup my downstairs stereo and a second stereo in my upstairs music room to accept streaming audio which I can access using a computer, tablet or smartphone.
My last purchase (or I’m going to start going to meetings…I’m an audiophile and I am helpless upon entering audio stores) is a set of Shure 535 in-ear monitors. I’m still getting used to them but there is a secret to putting them on. Use a mirror. It speeds up the process. They sound amazing.