A Journey Into Audiophile Headphones

10 minute read

One of the most powerful movie moments ever is the scene where Dorothy opens the door from a black & white world into color in The Wizard of Oz. It perfectly captures the feeling and experience of having your eyes opened to a perspective on the world that’s always been there, but you weren’t able to see.

We don’t live in a black and white world (at least visually), so we are unlikely to have the same type of eye opening experience as Dorothy. A few things might come close - The first time I saw an HD or 4K TV, a retina smartphone where the pixels were imperceptible or first time with Oculus Rift in a VR room were all little glimpses of this feeling. Still, the truth is our eyes have it pretty good already.

Our ears on the other hand, are often neglected. Not by quantity, but quality. We now have vast libraries of music such as Spotify, able to instantly access almost every song from the past 50 years. But when we press play, that music is often delivered to our ears with a tiny chip on our smartphones sending an under-amplified signal through a cheap pair of headphones. The aural world might as well be in black and white. But you don’t need a tornado to change the situation - just upgrade your headphones!


I begun my journey with a “starter” pair of headphones back about 10 years ago - the Shure E3c. These were a huge step up from standard ear buds, and lasted me a couple years, especially once I paired them with a set of triple flange ends to increase sound isolation.

The only problem with spending $200 on a pair of headphones and loving them, is you start to wonder; what if I’d spent $300 - What would that have gotten me? And so beings the inevitable escalation.


As I read on and learned more and more about what was out there, I was eventually tempted to make a jump up to something a little higher end - a pair of Shure SE425 ($300). The difference was quite profound, the 425s had much better low end, and overall sounded much richer. I was also doing some flying at the time for work as well as personal so I decided to invest in some Bose QuietComfort 2 noise cancelling headphones for $299. The QC2s are best described as $100 of headphones and $200 of noise cancellation. They certainly didn’t sound nearly as good as the Shure’s, but for flying or otherwise being in loud environments, these headphones are gold. Though they’ve continued to release newer and better models over the past years, it was the QC2s that first made noise cancellation really take off in a headphone product for also listening to music.

Still, despite loving what I had, I was still wondering if there was more out there if I just spent a little more. And there was.

High End

When I decided it was worth investing in a better pair of over-ear headphones. Some research lead me to the following components:

Total Cost $830

This was a giant step up in terms of quality and performance. Going with a separate DAC/AMP device let me power much a much more demanding set of headphones, that are ill-suited to be driven from a mobile phone for instance. Once upon a time the HD 650s were Sennheiser’s top of the line headphones, but they’ve since brought out various other higher end models such as the HD 800 S Everything about this setup sounded far better than what I’d previously been listening to.

This setup lasted me over 5 years. I thought it was as far as I’d go, but then I found myself at a Head-Fi meet-up surrounded by high end audio gear.

Jumping In Head-Fi(rst)

Head-Fi.org is arguably the best and post popular online headphone forum. But headphones are something you need to experience in person to fully appreciate. Thankfully they organize various local meet-ups where individual and vendors bring out all sorts of gear for people to come and try. I can’t say enough good things about this community - beyond enabling and encouraging me to spend thousands of dollars, they’re extremely knowledgeable and friendly. In 2015 I went to one in downtown San Francisco. I wasn’t quite sure what to expect, but it far exceeded any expectations. This thread has glorious pictures of all the gear.

My real Dorothy moment came at that meet-up when I first heard a true top of the line headphone setup. I put a pair of Hifiman HE-1000 headphones on my head, connected to a Schiit Yggdrasil DAC and Schiit Ragnarok amplifier, which all together cost about $7000, and pressed play on Hotel California (live from the Hell Freezes Over concert). I’d heard this song hundreds of times, it’s my reference track for listening to headphones or speakers, but this time I heard it in color. This was another level altogether, and inevitably attending this free event would end up costing me quite a lot of money.

The End Game

The meet-up was an amazing experience. I had the chance to try out many different types of headphones, source components, and amplifiers. Hearing the actual performance of these setups is so far above reading about them. This is of course the limitation of researching or discussing audio gear online - you can’t actually hear it. In the end I decided on the following components to make my new setup:

Total cost - $4500. High end speaker systems can cost tens of thousands of dollars. High end headphones can rival that sound for a fraction of that. So in a way, they’re affordable and a responsible choice - or at least that’s what I like to tell myself. So what comes next? Well, I could get into electrostatic headphones which are even more expensive, but I’ve heard them and don’t think they are quite enough of an improvement over what I’ve got to consider. Perhaps a top of the line pair of in-ear headphones, customized to my ears might be the next time my wallet is pried open.

Like many other types of things from cars to bicycles, the further you progress up the price scale the ever larger amounts you have to spend to notice appreciable differences, headphone audio gear also follows a logarithmic scale. I am certainly at a point of diminishing returns on further dollars spent.


Beyond my main setup, I’ve got various other headphones around for different situations.

  • Bose QuietComfort 20i - All the noise cancellation of their larger models in a in-ear portable form factor. These are my main everyday carry headphones. If you’re going to only invest in one single pair of headphones these are a must buy.
  • Bose QuietComfort 35 - Brand new bluetooth wireless version over-the-ear. I’ve only had them for a couple weeks but love them so far.
  • B&W P5 Wireless - Ok sound, but I bought these just months before the Bose QC35 was announced, meaning I’ll likely sell them soon.
  • Jaybird Bluebuds X - Bluetooth water resistant workout headphones, not the best sound but extremely functional. 1
  • PSB M4U 2 - When these came out I grabbed them and instantly sold my Bose QC2s. They are one of the best closed headphones out there. Fantastic sound, noise cancellation, mic for phone calls, and an internal amp.

A Golden Age

The headphone community has never been more vibrant, there have never been so many high end products available, and more and more people seem willing to spend big dollars on headphones. Part of the credit goes to the amazing marketing of Beats (originally by Dr. Dre, now owned by Apple). They convinced the mass market to spend a couple hundred dollars on headphones instead of relying on whatever cheap pair of earbuds came with the phone/ipod they use to play music on. More money being spent on headphones means more research and development dollars are spent on higher end technologies. However, despite their overall positive effect on the market, Beats headphones are universally looked down upon by the audiophile community as being poor in sound quality relative to their price. It’s relatively easy to troll headphone audiophiles by mentioning how your pair of Beats sounds better than whatever piece of equipment is being discussed.

Regardless of the origins, the suite of products in the headphone space has never been stronger. From affordable high quality items, right up to the ultra high end of electrostatics, from in ear to over the hear styles, the choices are nearly endless and can suit any budget, listening environment and style of music.

The Meta

Once you finish having your mind blown by the incredible audio experience a great setup can deliver, and get involved further in the community - you come to realize that a lot of being “into” headphones has little to do with listening to music. There is a meta.

Talking about Listening

The community has a vibrant vocabulary used to try and explain what something sounds like, without actually hearing it. Words like warmth, soundstage, and detailed, mean certain things. There are even glossaries around that can help you too sound like an audiophile.

Do Cables Matter?

There exist a whole bunch of people who are willing to spend large amounts of money on cables. Connector cables, headphone cables, even power cables, in pursuit of that perfect sound. There’s a famous story repeated around circles of people testing Monster Speaker Cables vs. Coat Hangers and finding no appreciable difference. Whatever your positions might be, there’s a surprising level of continuing dialog on the difference cables might or might not make. For what it’s worth, I used Monoprice cables for everything except my headphones where I ended up having to buy a custom cable to get the right length I wanted. It cost $290, yes, for just a cable.

High Resolution Audio

When listening to high end audio gear, you begin to notice that some recordings are a lot better than others - even if they might sound similar on lesser equipment. Beyond just the recording, there’s the format of the music recording. If it’s analog such as a vinyl record, then this doesn’t quite apply. But if it’s a digital file, there are also two main things to consider - the level of compression, and the resolution of the sampling to begin with. I won’t go into details because this becomes a partially scientific and partly philosophical argument. What is clear to me is that compression makes a big difference. There are many ways to test whether you can hear the difference between highly compressed MP3 music and “lossless” CD quality, such as this one from NPR. Beyond that there is the question of resolution. CDs began the digital music industry and used a sampling rate of 44kHz (44,000 samples per second) and 16 bits per sample. There are various other options now, up to 192kHz at 24 bits, and a completely different style altogether called DSD. Some say the higher resolution sounds better, and others say that anything above 44/16 is scientifically determined to be beyond the capabilities of the human ear to hear. For me, on good gear I can tell uncompressed from compressed but can’t determine any difference from resolutions above 44/16.

Where Has This Journey Led?

I’m sitting, plugged in listening to remastered Led Zeppelin tracks (which I bought in high resolution from HDTracks) reflecting on my experiences. These same songs I’ve listened to hundreds of times are now even more enjoyable than ever. I’ve also made new friends and gained an appreciation for both the craftsmanship of the vendors and the engagement of the enthusiasts. I think I have the desire for ever newer and better gear somewhat under control. There’s always the risk of going off the deep end but I think I’m more likely to reserve that kind of money for car purchases.

  1. I’d include a link, but they’ve been discontinued in favor of the X2