The Most Comfortable Headphones

Bose SoundTrue Ultra in-ear

In-ear headphones are designed to plug the ear canal, locking in every magnificent musical note while sealing out car horns, lunchroom chatter, and other unwanted noise pollution. But, for people sensitive to in-ear pressure, the headphones can be torturous. With this hybrid design from Bose, you get a shorter insert stabilized by a bowl-like earpiece and over-the-ear clip.

Although pricey, the headphones come with three pairs of earpieces to help you achieve the right fit and they remain securely in place, even during vigorous movement. Good news for headbangers!

For more recommendations, check out our headphone Ratings and buying guide.

Grado Prestige SR80e

Few things in life are more confining than a pair of home-style headphones. After a few tracks of Springsteen, you often find yourself wishing for a cool breeze to soothe your clammy ears. But, thanks to an open-air design, this inexpensive model from Grado allows for more ventilation than its closed counterparts. It also has a generous (though weighty) 80-inch cord that frees you up to dance around the room.

The plush foam pads are comfortable on the ears, but they won't block out all external noise. They'll let some sound escape, too, which means you may want to be careful when listening to Men at Work on the airplane. No need to let everyone know you have eclectic tastes.

Phiaton BT 100 NC

If you frequently find yourself getting tangled up in wires or ripping ear buds from your ears with an inadvertent snag, you may want to look into a pair of headphones such as these. The “collar” conceals a battery, antennae, and Bluetooth technology that lets you pair the unit wirelessly with a mobile device. This model also comes with earpieces in four different sizes to help you select the right fit.

While some music fans shy away from the collar's tech-nerd look, others love the way the design frees them from being tethered to their smartphones. Extra attributes: noise-canceling tech, convenient earbud storage in the collar, and a nice price compared to other models in this class.

Scosche SportClip 3

When you're bounding around the track or bending down to grab a barbell, the last thing you want is an earbud that keeps slipping from its perch. After all, it's hard to keep your heartrate up when you have to stop every few strides to fix your headphones.

This pair comes with bendable clips that secure the buds on your ears. It takes a little time to adjust them to the right fit, but once you do, you're off and running—with no excuse to stop. Splashproof and dustproof, Scosche's Sportclip also offers very good sound at a very nice price.