As I have previously mentioned, I buy a lot of running gear. Shoes, socks, shirts, iPods, watches and headphones. One thing I have not found is the perfect set of headphones. I have purchased maybe 10 pair of them, so much so that my 8 year old daughter commented "Daddy you always have the cooooolest headphones!" I also have several opinions. First and foremost, the "bud" type headphones generally do not stay in my ear when I run. That is the kind of headphones that comes with an iPod, and they just don't work for me. Second, my headphones have to be able to survive wetness. I sweat alot when I run, and my headphones get wet. Real wet. Sound quality is really not that important...I am running, not listening to a jazz. But, that being said, better sound is better. I honestly didn't notice sound quality differences in headphones until I had two pair of headphones that I liked and alternated. One pair was a cheap ($12) Koss pair, and the other was a pair of Sennheiser. The sound difference was both undeniable and incredible (the Sennheiser was maybe 50 times better). So my criteria are: fit and stay put-ness; durability; sound; and value.
The quest for the perfect headphone seems to endlessly continue, but my current favorites are the Sennheiser MX 85 Sport. Sennheiser is a generally upscale headphone manufacturer that also manufactures a sport line of headphones. They generally retail for around $50. They all sound noticeably better that bud type headphones, and are more expensive. Sennheiser's sport models come with distinctive colored cords: neon green and bright orange. They also have several headphone types: over the ear, ear plugs, around the neck (which I have not tried), and buds that "twist in place." My current favorites are the SX 85, orange cord, twist in place. Here is a picture:
The twist in place system really works. The headphones don't move around and stay put. And they are quite comfortable. They also have the best sound of the headphones I have tried and can notice. I sometimes run to military running cadences (Run to Navy Seals, if anyone listens) where an F16 flies over the recruits as they are singing. If you have ever experienced a flyover at a sporting event, you know this is an ear splitting, booming noise. The sound moves from left to right, and it never ceases to scare me, make me duck and I can feel it. The recruits are chanting "I wanna be a Navy Seal.." and then CRASHHHH BOOOOOM -- this massive sonic boom comes crashing through, in stereo, from left to right. It is pretty cool. Again, this is not an acoustic review of head phones, just what I perceive while running. The Sennheisers make me feel it.
Other Senneheiser thoughts. First, the orange cord version is a huge improvement over the green cord. The green cord came precoiled and never uncoiled -- it was like a big green slinky. A massive inconvenience. The orange cord is better.
The cord will tangle. Period. Dig out your Boy Scout manual because you will become a knot expert. There is nothing you can do about it. Nothing. If you set them down, massive tangle; put them in a gym bag, massive tangle; speak badly about them, massive tangle; look at them, massive tangle. But, once untangled, they stay in your ear and sound good. Durability is OK. I suppose I should wash them, dry them, etc. but they are headphones, and I don't want high maintenance there.
Other headphones I like: V Moda Bass Freq Earbuds; Philips Ear Buds (Bass)