Just to update this thread, in case it’s useful for anyone else… I found a good solution:
They do exactly what I wanted - stay in place while running, no more faffing around all the time.
Ironically enough, I almost answered my own question right at the start with, “Thanks for any tips!”
You must give a try to Bone conduction headphones.
opt for lightweight, secure, and sweatproof headphones. The Drip-fly Oz5 is a good choice with an IPX8 rating, 32GB MP3 storage, and a unique bendable design for open-ear or in-ear use. Alternatives like Shokz OpenRun or Jabra Elite Active 75t also offer great comfort and sound quality…
1st off I’m not running in “cans” I tried it once when the cable snapped on my wired ear buds and I borrowed my daughters SONY WH-CH520 wireless headphones. Never again, a disgusting amount of Holy Water was produced and I felt ashamed to return them to her.
2nd I’m a luddite, why faff with pairing Bluetooth when a 3.5mm jack pairs perfectly every time and there is no battery to remember to charge. I find that cables last about 5 years before the wire fatigues, breaks and loses connection. Do wireless buds last that long?
I’ve never found an in-ear bud that stays in reliably, so I always pick a style with a hook or over ear loop.
I’m currently using MEE Audio M6 In-Ear Sports Headphones with Memory Wire, they came with 6 sizes and shapes of eartips, they sound great, fit well, the only downside is the cable is crazy long at 130cm.