Save $10 on these waterproof Plantronics BackBeat FIT 2100 wireless headphones. They are great running headphones because they not only fit securely around your ear, but also inside your ear using soft, flexible eartips. The neckband lays gently on the back of your neck, so it doesn't pull down on the actual headphones. Within the companion app on your smartphone you can also customize tappable features on the headphones using what they call My Tap—one tap could be to pause, and two taps could be set to switch the song. These headphones hold a seven-hour charge and have a reflective finish, making it safer to run at night. $60.