Top Pick
On Sale
Powerbeats Pro Totally Wireless Earphones
Powerbeats Pro Totally Wireless Earphones
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The Powerbeats Pro is the complete package—both well-rounded as wireless sport headphones and literally a large box that contains the earbuds and an additional 15 hours of juice. Not that you’re likely to need it; the buds last for 9 hours on a single charge. Bluetooth pairing is immediate with an iPhone and a 5-minute quick charge delivers 90 minutes of playback. They’re rated IPX4 so they'll withstand a rainstorm (but not submersion), and despite their large appearance, the buds keep a low enough profile to be comfortable with a hat and sunglasses.

Best Wire-Connected 'Buds
JBL Reflect Mini 2.0
JBL Reflect Mini 2.0

There’s a lot to like in these popular ear buds: The buds form a tight seal in your ears and don’t move after you’ve started to trot. The downside for outdoor runners is the lack of ambient sound, which also isolates your tunes from the outside world. The connecting wire between the buds is lightweight and hardly noticeable mid-run, and the Reflect Mini 2 connected via Bluetooth fast and, outdoors, it stayed connected up to 100 feet away. The earbuds also sport reflective cables for nighttime visibility, an IPX5 water-resistant rating, and an impressive 10 hours of battery life.

Most Durable Ear Buds
On Sale
Jaybird Vista 2
Jaybird Vista 2

Three interchangeable silicone ear gels ensure you get the most comfortable fit, and once they're in, they stay in place. They're durable to the point that they have military-grade standards, and they're dustproof, sweat proof, and waterproof up to five feet deep for 30 minutes. Plus, you'll get eight hours of playtime on a full charge, and a quick five-minute charge gives you an hour.

Budget Buy
On Sale
Anker Soundcore Spirit Pro Wireless Headphones
Anker Soundcore Spirit Pro Wireless Headphones

Waterproof and sweatproof, these headphones are about to be your new workout partner of choice. With extra bass, a selection of ear tips and ear wings, and up to 10 hours of play time, they keep your playlist and your workout on track. And if you get a call, hands-free answering won't interrupt your workout.

Best For Awareness
On Sale
AfterShokz Air Open-Ear Wireless Headphones
AfterShokz Air Open-Ear Wireless Headphones

For road runners who aren’t comfortable jamming an earbud into their ear as cars whiz past, there’s the Aftershokz Trekz Air. These headphones use bone conduction technology to transfer sound through your cheekbones, leaving your ears open to hear potential hazards before they sneak up on you. The headband is lighter and slimmer than the previous model, which allows you to wear sunglasses with the headphones. A 6-hour battery life and a sweat-resistant IP55 rating puts the Trekz Air on-par with truly wireless buds of a similar price—you’re losing an in-ear headphone’s full sound, but gaining total awareness.