I got Shokz Openrun Pro after dealing with a couple of shit pairs: everything falls out of my weirdly shaped earholes. I was worried about the band around the back, but I don’t even notice it. Because they’re bone conduction, they leave my ears open and I can hear cars or bike bells. My favourite bit is that I can wear them with earplugs when I mow the lawn and still hear music.

Tbh, this is a time when sound quality takes a back seat to design.

Now, a caveat, I’m not a runner, I’m disabled. So I do strength training upper body work, and water based exercise. There’s not as much impact, so I can’t promise that won’t be a factor.

But I’ve tried a handful of Bluetooth buds because of the sweating and pool use. JBL makes or made a model called “reflect flow”.

The controls are built so that it takes a firm push to activate them, so no issues with sweat or other water triggering them. They’re even functional with a device in a protective baggie, and my head under water a good bit. Not deep, but submerged, or while swimming. It’s one of those ymmv things though, as Bluetooth in general isn’t great at penetrating water of any depth.

Sound is what I’d call acceptable. Not great, but vocals are clear enough to pick out words with no issues while moving through water, or in a gym full of people clanking weights. Can’t match wired IEMs, but I doubt that’s the goal. They run a tad bass heavy, and the highs can get dampened more than I’d like, but not unexpectedly so.

But the controls have never, ever triggered unless I pushed them. The case is solid, and keeps a charge well even after about five years of use (iirc, could be off by a year either way since I was borrowing before buying, and can’t recall which brands I tried when). They aren’t expensive either, which considering that Bluetooth earbuds are essentially unrepairable is a good thing.

I’d give them an overall 7/10 for sound, 10/10 for waterproofing, and 10/10 for both battery lives. My standard for a 10/10 sound is my beyerdynamic 770s though, which isn’t everyone’s preference. Tin t2s are a solid 9/10 for sound to my ears. Just for a sense of how I judge sound on fairly common budget choices in wired audio.

Have you looked at bone conduction ear buds? I don’t run anymore and never had a pair, but when I was in the community they seemed like the only type worth getting

I have Jabra elite 85s I think it’s the model. They’re great

I wear Sony Linkbuds while running or cycling. They have a hole in the middle which means they have basically no sound isolation at all, making them very safe to use if you’re running on the road or footpath where motor vehicles or cyclists might come up behind you. The open design also allows you to hear your breathing properly and it you won’t get that annoying heartbeat/pulse effect where the sound ducks in and out like you do with closed in-ear earphones. They don’t go into your ear canal, but rather sit outside like the classic Apple earphones or Galaxy Buds Live. They have an IPX4 rating which means:

Water splashing against the enclosure from any direction shall have no harmful effect, utilizing either:

a) an oscillating fixture, or b) A spray nozzle with no shield. Test a) is conducted for 10 minutes. b) is conducted (without shield) for 5 minutes minimum.

They also have a feature called wide area tap, which (when enabled) extends the touch controls out along your cheek bones. Instead of tapping the earphones themselves, you can tap on your face instead to control them. I find this extremely useful while running or cycling, because it requires far less precision and works reliably in any weather conditions without dislodging the earphones.

I don’t use them for serious listening too often, so I haven’t paid great attention to the audio quality, but to me they sound fairly balanced for consumer earphones with a nice level of detail and a slightly wider soundstage because of the open design. The battery life for both the earphones and the case is also good. The only major problem with them is the fit - you will need to experiment with the wings to find a combination that fits your ear shape and some people have reported that they just won’t stay in their ears. The wings can also make them uncomfortable after longer periods (several hours) though I rarely wear them for over an hour at a time so this doesn’t bother me too much.

Overall I’d say they’re much more a competitor to bone conduction headphones than typical earphones. They have a significantly smaller profile than bone conduction models and better sound, plus they don’t look as cringe. Here are a couple of runners reviewing them if you’re interested. I bought mine refurbished from the official Sony eBay store for a significant discount, so it might be worth checking for that too.

I just bought my second pair of Soundcore Sport X-series. I have a pair of X10’s that I’ve used for several years, but decides to buy a new pair of X20’s. The quality is great, the mic is good, you can use the phone app to adjust levels and they have a small ear loop to go over/behind to help keep them in place when moving around.

I always wear bone conducting headphones when running. Need to hear alle the electrical scooters that try to kill me.

I opted for Shokz Openrun instead of the pro model. Mainly because of the higher IP rating. Sweath, rain and snow no worries anymore. I han a set of Shokz Openmove earlier, that eventually died from water. But Openrun is fantastic.

I find the sound quality pretty good, but a bit lacking in bass. Be aware that the wind noise makes them less fitting for riding a bike, unless you cover your ears with a helmet cap or something similar.

i’ve just switched to a wired usb-c option. it’s a fraction of the cost, water- and dust-resistant by it’s very nature, and i don’t have to worry about forgetting to recharge their “batteries”.

just tuck the cable into the neck hole and dangle it through the bottom of the t-shirt to the phone and bob’s your uncle.

i got them after a set of airpods and two sets of bose earbuds crapped out on me and i haven’t regretted the decision yet.

As a decade long, all season all weather bike commuter, I can attest that the Plantronics line of sport headphones have worked well for me. They are designed to be waterproof, and allow for background noise to be very noticeable (specifically NOT noise cancelling which is incredibly important when you’re out in traffic). They have a line that are individual buds, or a wrap around version (both have the same in-ear design that hook around your earlobe). I have and use both versions and have no complaints. There are probably better headphones out there but these fit that use case perfectly in my mind.

The Beats Fit Pros are nice. I don’t do a ton of exercise in them but think they’d handle all the issues you mentioned pretty well.