I can’t use in ear or buds, they just fall out of my weird ears. So I am after advice for wireless on ear headphones. They need to fit tight as I have a small head. I bought a cheap pair from Amazon and with one shake of the head they fell off so got sent back. Budget of around £50 so I don’t cry if they get broken or fail after a really wet run. What does the hive mind here recommend please?

Try Aftershox , they are brilliant.

I had similar problems with ear buds and went with a cheap wireless option from MPOW and they’ve been brilliant. Sound is more than good enough for running with, battery life is excellent and the connecting cable means in the unlikely event you knock one from an ear, it’s still easy to find it/them.
Headphones

Those Mpow look worth a crack at £20. Ordered and will see if they stay in place with a head shake

Bit late, but I use a single ear bud with a Comply foam ear tip whilst running, these expand and seem to grip tight, also wearing just a single bud means I can hear traffic and ‘bloody cyclists’ as they try to pass me 😉

Never too late… I’m still open to ideas in case the Mpow ones aren’t right. I’d still prefer on ear with a proper headband if they don’t work out

Second Aftershox, take a little getting used to simply because you end up amazed how they work.

Picked up the Mpow ones. Subjected to the highly scientific head shake test and straight off the ears so back to the drawing board. Aftershokz are a little more than I want/can afford to spend. Think I’m going to save up a little if I can and use my old wired Beats Solo for a bit longer. Don’t want to ruin my good Sennheiser headphones with sweat and rain

I’ve some Mee audio in ear but with an over ear mouldable wire – they have stayed put much, much better than anything else I’ve tried. You can mould the wire to actually maintain an inward pressure on the ear bud.

I’ve used Koss Sporta-Pro with a cheap blue tooth receiver for many many years.
Stay put, comfy, and unlimited lifetime warranty. Yes, twice I have broken mine, and they were replaced without question.

I bought my gf some of these which she uses for running and also insomnia.
She really likes them a lot but says in summer they might get a bit warm.

Bluetooth headband headphones