Scosche's IEM856 In-Ear Monitors give a rich, deep-sounding quality, travel well, and have become one of my go-to headphone choices this year. Credit the sound quality to the same kind of dynamic driver/balanced armature combination found in many high-end headphones, which gives you booming bass, crisp highs, and everything in between. The IEM865s are built tough to stand up to lots of jamming into and out of pockets and carry-ons, and the thick, linguine-shaped cord, which resists tangling and is as strong as any cable here, has a great oversize volume control. (The same flat cord can be found on a-Jays Four earphones from Jays, which go for $70.) Admittedly, they're not cheap, but you can find them online for a fraction of the sticker price.
A lot of brands these days are touting their noise-isolating technologies, which in most cases is a “passive” form of blocking noise—that is, headphones with lots of insulation, or in-ear phones that create a seal, like earplugs, and voilà: less external noise. Bose is one of the only companies to use active noise cancellation, which detects incoming noise and emits an inverse signal to literally cancel it out. (Both types of technology allow you to listen at lower volumes, which is better for the health of your ears.) If you’ve ever worn Bose’s now legendary QuietComfort headphones on a plane, you'll immediately hear the difference. The high-pitched drones of jet engines and crying babies fall away, letting you enjoy a quiet podcast or violin concerto as if you were lying in bed. That said, $300 (plus two AAA batteries) is a lot to drop on something you can accidentally leave behind in the seat pocket—so don’t leave them behind in the seat pocket. (Do I sound angry at myself?) Still, bring these on an overnight flight to Europe (just turn them on and play silence) and you'll remember why God made headphones.
Only good skiers should listen to tunes, which rules me out. So I polled my skier friends, who say that, with the cord tucked inside your coat and the earbuds tucked under your headwear, a secure fit is less important than durability and the ability to control volume with gloves on. And given the abuse headphones will endure on the mountain—snow, sweat, and cold—investing a lot of money probably isn't the way to go. For above-average sound in a cheap, waterproof package, Logitech's Ultimate Ears 200 Noise-Isolating Headset is hard to beat. It has an inline volume control and mic, letting you answer important calls, like buddies summoning you to the lodge for lunch. Noise isolation is a mixed bag, however: you'll get better sound quality at a lower volume, but you're less likely to hear someone coming up behind you. If that makes you nervous, the standard earbuds that come with iPods and iPhones will do.
Headphones from Beats by Dr. Dre and Skullcandy are popular, but in the event of a wipeout, V-Moda's Crossfade M-80 are what you'll want. Built to military specifications from Kevlar and steel, these are likely the toughest headphones in the world: they're rated for extreme high and low temps, can absorb multiple drops from six feet and up, and won't yield to yanking and bending. Acoustically, they’ll also surpass most other models, with rich, symphonic sound and enough bass to satisfy hip-hop lovers. And for $25, you can customize the outer “shields” with your own art. If you expect lots of falls, protect your player or phone, too, with an OtterBox case (from $20).
I'm not a huge fan of listening to music while I ride, but when I do, on lonesome stretches of road or trail, I use JayBird Gear's Bluetooth-equipped Freedom earbuds. They stay in place, and, because they're wireless, I never have to stop to make adjustments (or, worse, and adjust on the fly). They’re also a good pick for runners, though jostling can make the connection choppy when the batteries near their six-hour limit. As with all Bluetooth-enabled headphones, the sound quality isn't top-notch, but if you get the fit right (there are multiple tip sizes, and wetting them helps), they’ll bring out enough bass to keep most listeners happy. Volume controlls are on the right earpiece, and I've found that a pair of Slipstreamz ($25), which are a bit like spoilers for your ears, reduce wind noise and let you hear approaching cars.