Best Running Headphones

The best headphones for running will sound good, stay in place, last long enough, block wind noise, and be comfortable. As an iPhone user, I've tried several options, and none are perfect, so here are the pros and cons.

1 Apple AirPods Pro (2nd Generation)

The Apple AirPods Pro are noise cancellation in ear headphones that are my preferred option for windy conditions.

• Good enough noise cancellation, including wind noise. The also include "conversation awareness", so if you start speaking it will stop noise cancellation.
• The battery life is sufficient for most runners, but 5 hours is a bit limited for ultrarunning. The case is sweatproof, so you could carry the case and recharge part way through the run, but that's rather grim.
• The lack of hooks means these earbuds fall out too easily unless you're wearing a hat that holds them in place. You can buy aftermarket hooks, but that's a kludge given how expensive they are.
• The controls are way too fiddly to use when running, and it's easy to dislodge a bud and drop it.
• With an iPhone, support for "hey siri" makes voice control an option, though I've not found it as reliable as the Powerbeats Pro.
• The AirPods are waterproof enough for running in the rain.

2 Beats Powerbeats Pro

Without any wind, the Powerbeats Pro are nearly ideal for iPhone runners.

• Even slight air movements seem to be amplified by the Powerbeats Pro, making wind noise quite painful at time. Covering them with a fleece hat reduces the wind noise but doesn't eliminate it. And a warm hat is obviously not an option in hot conditions.
• The ear hooks mean the earbuds won't fall out and keep them positioned in the ear.
• The sound quality is great, but the lack of noise cancellation and the amplification of wind makes it hard to get the best quality.
• I found the controls easy to use when running, even wearing thin gloves. The "hey siri" works well, and combined with Apple Music makes voice control easy.
• The battery life is good enough for most runners, even moderate ultradistance, lasting up to 9 hours.
• The Powerbeats Pro are waterproof enough for running in the rain, but the case is not waterproof so you can't easily take it with you on a run. The case is a bit big for carrying, even in a pack, so the lack of waterproof probably isn't an issue.

3 Shokz Openrun Pro

These bone conduction headphones are an alternative to typical earbuds.

• I find that compared with the AirPods or Powerbeats, the sound quality is quite poor. It's thin and imprecise, even in quiet environments.
• Being bone conduction, there's no blocking of ambient sound, which can be handy in some situations where you want situational awareness. The ambient sound is more natural than the AirPods in ambient passthrough mode, but the AirPods allow for a nice mix of noise cancelation and awareness.
• Sometimes the pressure points for the Shokz can upset my jaw muscles, making them ache. I also don't find they fit well under warm hats.
• The controls are better than the Airpods, but no where near as good as the Powerbeats. I can find the Shokz controls, but I don't find it as easy as I'd like.
• The battery lasts 10 hours, so that should be enough for most runners, and they're waterproof enough for running.
• You can use the Shokz with ear plugs to block out wind and ambient noise, but this results in the sound becoming overly booming and muffled. Changing the audio mode to voice helps a bit, but still the quality isn't great.
• There's no "hey siri" support, and the microphone doesn't seem good enough for dictation.

4 Apple Earbuds

The cheap earbuds that come with an iPhone are my backup for when the battery dies on longer runs. They work surprisingly well given their low cost.

5 Koss Portapro/Sportapro

These are old school wired headphones that are comfortable and sound great. They're too bulky to use as a backup, and having got used to true wireless earbuds, it's hard to go back.