Your arms pump as your feet glide across the pavement, the effortless movement of a good run. Light beads of sweat build on your skin and fly off in the wind. This wonderful exertion can be interrupted by a dog, a car or a stoplight. But those are out of your control. We hate when headphones falling out, something we can control, interrupts our run. We've decided to do something about it. These are the options we're exploring for keeping the runner's high going...
There are many qualities that make a good running headphone. The first is obviously that they fit snugly without hurting after, or especially during, a run. The next is isolation. While some like to block out all noise on their runs to minimize the need to blast the volume and to get lost in their run, we like a little less than perfect noise canceling in order to maintain sensory awareness nobody wants to get hit by a car. We also don't want to hear headache inducing noises every time the cable hits our shirt. The last quality we're looking for in a running headphone is sound quality. While we're not looking for the awe-inspiring sound like you'd find in at-home, over-the-ear sets, but we also don't want our music or podcasts to sound like they're coming from a tin can on a string. There are three types of headphones that seem to achieve these qualities.
1. Wrap Around
These remind us of the headphones that used to come with the old JVC and Sony portable CD players. Man were you cool if you had one of those velcro-ed to your hand on a jog. Headphones of this variety wrap around the back of your head and fit snugly in your ears using the elasticity of the band. A good pair will have proper shape for the ears and padding to boot. Our one complaint with these is we can't seem to find a decent pair that we can wear our sunglasses with. Sound quality in general seems to be better than most earbuds and isolation is mostly passive, meaning no noises with the wind and the ability to hear around us at a reasonable volume. The one pictured above are the Sennheiser PMX70s ($44.95), a line of headphones that have gotten rave reviews from runners on the net, especially the Runner's World forums. We've also heard good things about the Philips SHS5200/28 ($13.23) and the lesser-known MEElectronics M6 ($20.84).
2. Specialized Earbuds
Earbuds are the best minimal option for running, and we do like the less is more approach, but sometimes less is just less. Case in point being the low-end jelly stuff you find in the bargain bin at your local pharmacy or the painful noises you get when the cable on a cheap pair of the low-end Skullcandy's brushes your shirt. The best earbuds for running are often ones modified with rubber or foam to keep the speaker comfortably stable in your ear even after you sweat. We've heard good things about Yurbuds ($45), the ones shown above, as well as ComplyFoam ($9.95-19.95) as an add-on to your existing pair. We also have some other reviews of earbuds that stay in.
3. Bluetooth
We gave these a separate category because they tend to be bulkier than the cable variety and that's certainly a consideration you don't have to worry about with most headphones. They do, however, provide the ability to run with less of a chance of yanking your headphones out of your head. Pictured above are Freedoms by Jaybird ($99). Plantronics 903+ ($48.45) and Motorola S10-HDs ($56.22) also look like good options. If we could find a small blue tooth receiver, we'd thinking of pairing these with an iPod nano watch and some Nike+ for truly lightweight running.
Have any experience with these or other headphones for running? Help us find the best solution in the comments.
(Images: Yurbuds, Jaybird and Flickr users KaiChanVong, lululemon athletica, Sochie and under creative commons.)

Shaw's Original Fir...
After trying various running headphones, the big winner for me ended up being the Sennheiser MX 85. After a quick Google, you'll see that these are "Twist to Fit" which means they fit very snugly in your ears. The downside is that your ears may be uncomfortable for the first few runs while adjusting to the buds, but this discomfort is really a testament to just how difficult it would be to shake them loose. They come with various rubber 'knobs' so you can find the right fit for you.
Also, since this is an ear bud, and doesn't enter the ear canal, you can hear any sounds around you. The cord is thick and rubberized, but doesn't resonate "thumping" like the author mentioned above. As a bonus the whole thing is highly water resistant. While I wouldn't recommend swimming in them, I have run in the rain, and rinsed my sweat off them many times without negative effects.
I don't run, but I do snowboard, and I have never had any luck with ear buds, and the looseness of wrap around headphones make me nervous. I bought a pair of Sony MDR AS20J a few years ago, and I love them. The sound quality isn't great, but they're cheap, and stay put because of the over the ear loop.
I love my plantonics 903's. Use them running, hitting the heavy bag, even use them mowing the lawn. They also work great for pc gaming with a bluetooth receiver. I had the Sennheisers and haven't touched them since I got the 903's
I recently had a pair of "sweat" proof headphones (wrap type from Sennheiser) die on me, and ended up buying a pair H2OAudio branded over the ear models. They sell them as water proof, including swimming, and so far, so good - although they are *extremely* sound isolating!
I actually use a square of surgical tape over my ear-buds, anchored to the folds of my ears to keep them in. I usually get sweaty enough that the tape pulls away easily without taking my ear with it, but I've never had an earbud fall out with the tape on.
try these: http://www.amazon.com/gp/product/B003DTLV8K/ref=wms_ohs_product there is a reason they are so popular on amazon. Bonus - you can pick up calls with it because it is a full headset.
I got the sennheiser/adidas 680 sport earbuds. The little "wings" bothered my ears a little at first, but they're pretty comfy for an hour now, and they stay put!
I always wonder why lower-end etymotics never get mentioned in discussions about in-ear headphones. I've used these for years, they sound great, and they definitely stay in. The only caveat being that they can clog requiring filter replacement.