My friend Jon Callaghan asked me what I recommended in terms of audiophile headphones, so I thought I’d share my answer with the world here under the Ask Matt category. I use three headphones on a regular basis, and they fall pretty nicely into low, mid, a high-end. There’s a super-high end I’m not going to cover here, because once you get into the world of headphones requiring amps you might as well just build a good open air system. I’ve tried probably two dozen headphones ranging from $50 to $1,200.

When I’m walking around on the street with my iPhone, my everyday buds are the step-up Apple In-Ear headphones, which come in around $80. They have a sweet triangle carrying case which makes them compact in my bag, and as a bonus the mic/volume remote thing works great with the 3GS, so I seldom take my phone out of my pocket. It’s also handy if you get a call, people have told me the voice quality is significantly better than calls I do on the cheapie included iPhone headphones, which always fell out of my ears too. They’re also easy to share with someone. So that’s my everyday pick.

If I’m listening to headphones at home or for a long period, I’m not a fan of in-ears because they aren’t as comfortable and my ears get “waxy” after more than about an hour. The most comfortable, best sounding, and least hassle headphones I’ve found for everyday use are the Sennheiser HD-595s, which I believe I discovered through Jeremy Zawodny. They’re big and bulky, and the cord is really long, but they’re just so darn comfortable. You can wear these all day and not mind at all. The price point is around $185–$220 on Amazon, which I linked above and I feel is an excellent value.

My final category of usage is travel, particularly on airplanes, where I want the highest fidelity, comfort, and sound isolation. Honestly in price point there’s a dead zone between around $250–$900, including all the Shures which I’ve tried and would not recommend anymore. (I used to be a Shure fan and have used their entire range.) This was the hardest category for me to crack, I tried various sound-cancellation models, but ultimately felt like they distorted the sound.

I finally ended up going with Ultimate Ear Custom line, first the UE-10 and later the UE-11. Now these are a bit of an experience, so let me walk you through what happens when you buy them. First you choose your options on the website, I’d recommend going all-clear for cord and buds, otherwise they look a bit weird. I’ve had both the 64 inch and 48 inch cord — the 48 is about exactly enough to go under a jacket and from your waist to your ears, but doesn’t give you a lot of room otherwise. I have the 64 inch now and the extra inches give me more flexibility and don’t get in the way.

So you go to the website, take out a second mortgage, and plop down $900 for the UE-10 or $1,150 for the UE-11. They then point you to a local ear specialist, which basically means someplace that does hearing aids, where they will make a mold of your ear. (Though the second time I did this it was at a cool rock and roll place in San Francisco. UE keep your molds on file, but apparently the shape changes and if it’s been more than a year you should get new ones made.) This is usually pretty cheap, and they’ll mail the molds directly to Ultimate Ears with your information. A few weeks later, your headphones show up in a fancy metal box, which now I think they put your name on.

I first got the UE-10s probably 5 years ago and the cost was really prohibitive, but then I realized that I had spent almost that much on a series of crappy headphones that kept breaking. They are also like a first-class upgrade on every flight — I’ve literally been sitting next to a crying baby in the back seat of economy and these headphones blocked the entire thing out. Close your eyes and let the music take you someplace else. They work so well because they fit your ear perfectly, so create a seal that blocks external noise, rather than having to juggle the sound to compensate like noise-canceling headphones do.

The Ultimate Ears have a feature where the cord pulls out of the buds if they get yanked really hard, presumably to prevent damage to your ear. Because I had gotten the shorter cord I kept doing this, and eventually (4 years in) I had done this so many times they didn’t really stay together properly and I kept dropping them. They also got a lot of abuse in my bag. Their ultimate demise was after I had dropped them the hundredth time and actually stepped on them, shattering the hard plastic mold. I probably could have gotten them repaired, but they were pretty far gone and decided to go for an upgrade instead for just a bit more, the UE-11s.

In the 4 years or so between my two purchases, UE definitely made some improvements to the line. The cord was thinner, didn’t have a wrap, and didn’t seem to tangle as much. The new ones came with a nice carrying case that if I had before I might not have broken the old ones so much. I’ve also never had a problem with the cord coming out like I did before. I talked Toni into the UE-10s and his new ones had all the same fit and finish. Unfortunately, don’t think the audio quality difference between the two warranted the $250 price difference.  I’ve been using them about 8 months, and they’ve travelled with me hundreds of thousands of miles around the globe. Overall the UE-11s just feel a bit heavier on the bass, but not really noticeably better than the UE-10s. If in 5 years I’m buying another pair I’ll go back to the UE-10s. A downside, or upside, of the Ultimate Ear Customs is no one else can use them.

My last bit of advice is to avoid everything Bose.

I’m curious what other people have tried, and what has been the best.