As someone also preferring headphones to in-ears for the same reasons, have you tried something like the shokz openrun series? The audio quality isn't the best, but your ears are free. Otherwise I'd suggest trying dry shampoo or other quick hair styling tools and just accept headphone hair instead lol. Nothing smaller than a headphone can ever come close enough for an audiophile.

You might look at "clip on" earbuds. It's a new form factor in the past few years that doesn't have a part that goes in the canal

I’ve compared many EarPods over the years, and Bose turned out to be the best (sound and fit). (They have one disadvantage: if you mention Bose, you will immediately get pummeled, it’s a “thing” with some people).

I have sensitive ears as well and got some bone conduction headphones. They sound all right for me and nothing sits in the ear and you can still hear what's going on around you as long as they are not too loud. Perfect for riding my bike.

They are called Shox, but there are different brands.

Try behind the head headphones. The bans rides at the back base of your head.

I've got some insane ear canals. Something about both size and shape that makes very small plugs fall out and medium to large plugs hurt (and rarely an earbud brand has one that doesn't hurt and doesn't fall out). The ear doctor didn't have any plugs small enough for me for the sound test machine. But Beyerdynamic Amiron 300 fits perfectly, I think it was the small, not XS that worked for me. Maybe give that one a test in a store if possible.

there are a lot of in ears with interchangeable tips. they typically come with S, M, and L sizes

I use the Soundcore v30i. They dont go in the ear itself - they loop around the back of the ear and are very light. I wear them for 7 hours a day most days and often forget they are on.

I dont know much about sound quality ratings, but I rather like them! (They are also pretty cheap and the battery life is quite good)

I really like KZ earbuds because they're so much better than slop audio consumer equipment but they're basically giving them away. KZ EDX Pro I got for literally [mathing] 7 or 8 USD (?) and they're amazing for running

I would say try open earbuds but those don't really have ANC

If you do want to try, clip on earbuds might work. They don't really sit in the canal, so your ear doesn't hurt. I have the moondrop collab ones

https://youtu.be/yJ5kAWedgNs

If you like headphones then clip on ones might work for you. Those are usually wired though

https://youtu.be/9lSINIxNmt8

Different companies may not ship to where you live so my suggestion is to search for molded or moldable earbuds.

You can get some high quality ones if you have cash to burn, and some that will be okay and stay in place for a lower budget.

Not the best solution but can the silicon ear bud part be taken out or replaced? Some in-ear earphones can still stay in place even with the silicon part off but the sound quality might be worse and they are less securely fitted to the ears.

Huawei freeclip

I don't know if this would solve your problem, but I would try getting a pair of replacement foam ear tips for your earbuds of choice. I always buy the Comply foam ear tips. They come in S/M/L sizes and they make them to fit most ear buds.

I don't have extra small ear canals, I just prefer them.

https://www.amazon.com/Koss-KSC75-Portable-Stereophone-Headphones/dp/B0006B486K

They may or may not be right for you, but the sound is way better than the price tag, and the price is low enough to be worth trying them. They have a Bluetooth version as well. No anc though. They're as comfortable as it gets for clip ons.

Thing with buds is that you gotta find the right tips. Comply is the default brand because they make something to fit every damn size out there. So you may just need to hunt down new tips instead

There are these soft clip-on earphones I use that look almost like ultra thicc earrings, they're pretty comfortable. I used to be an over-ear earphone cultist but these are much more comfortable.

Edit: found em

You need to get a big pack of replacement buds of all sizes. Start with a pair slightly too big for your ears until that becomes comfortable, then transition to the next size up. Repeat.

Do they still make the ones you warm up in water and push in to custom fit your ears? I knew someone who had one like that and it was apparently quite comfortable.