1. Jaybird X3
These are superb running headphone, and are extremely reasonably priced given the features on offer. They don't boast a huge range of controls, but they're comfortable, lightweight and sweatproof. The security of the fit on offer is best-in-class, too, which matters a lot when you're working out vigorously. With a good charging case into the mix, taking the earbuds' six-hour battery life up to 16 hours without needing main power, and really decent sound, too, the Vista marks a genuinely impressive effort from the ever-improving Jaybird.
2. Beats Powerbeats Pro
Water-resistant: Yes (IPX4 rating -- splashproof). Yes, the Beats Powerbeats Pro's jumbo charging case is a notable drawback. But the combination of incorporating all the features that make Apple's AirPods great while delivering richer sound quality and better battery life in a wireless earbuds design that won't fall out of your ear (ear hooks for the win!) ultimately is a winning proposition for earbuds for running. Just make sure you buy these running earbuds somewhere that has a good return policy in case you're in the small minority that has ears that aren't quite a match for the buds. Note that these headphones are frequently reduced from $250 to $200 -- don't pay more than that if you're buying them.
3. Apple AirPods Pro
Water-resistant: Yes (IPX4 rating -- splashproof). Even if they don't sound quite as magical as you'd hope a $249 model would, the AirPods Pro still manage to be a great pair of truly wireless headphones for running. That's largely due to their winning design and fit, improved bass performance, effective noise cancellation and excellent call quality. While I can't run with the standard AirPods (those in-ear headphones don't fit my ears securely), I had no trouble running with the AirPods Pro, which have a noise-isolating design with a silicone tip that sits snugly in your ear.
4. Bose SoundSport Wireless
Water-resistant: Yes (IPX4 rating -- splashproof). Bose's totally wireless earphones, the SoundSport Free (the true wireless earbuds version of the SoundSport Pulse), are comfortable to wear and deliver excellent sound for true wireless. These SoundSport wireless headphones have a few small downsides (both the wireless earbuds and carrying case are a bit big), but they have a secure fit, work reliably, and are water-resistant. Note that Bose will be bringing out its next-generation true wireless headphones -- the Earbuds 500 -- in early 2020.
5. JBL Reflect Flow
JBL is a heavy hitter when it comes to sports earphones and the JBL Reflect Flow is a hotly anticipated entrant to the flourishing, albeit rather niche, true-wireless-for-sports market. In their niche category, though, the JBL Reflect Flow headphones impressive performers for the money, especially if you want a bass-heavy sound for the gym without resorting to a pair of over-ear headphones – and the 10-hour battery (or 30 with the case) will outlast a seriously long gym session. There are better wireless earbuds for pure sonic performance but if you want a sporty option, these might just be the best bet.
6. Jabra Elite Active 75t
An all-around performer that hits every mark, the Elite Active 75t currently stands as the best sport headphones for working out. Jabra somehow managed to scale down the design, while increasing battery life (7.5 hours per charge, 28 hours with charging case) and the IPX rating (IP57), making these buds waterproof, dust- and sweat-resistant. Even with its smaller form, the Elite Active 75t affords great comfort and on-ear stability. You’ll also enjoy the same vibrant audio associated with the Elite series, only this time the bass has been fine-tuned to achieve full, detailed sound. And that is just scratching the Elite Active 75t’s near-indestructible surface.