This thread sent me down a rabbit hole and I might as well share what I've learned. I do think it's highly personable based on anatomy of your ear and such.
I first bought the Sony buds. Highly rated for sound and as I said upthread I have the equivalent over-ear and they are amazing and extremely comfortable.
Sony WF-1000XM4 Industry Leading Noise Canceling Truly Wireless Earbud Headphones with Alexa Built-in, Black https://a.co/d/2jVB7XX
These sounded really good to me but were bulky and not comfortable. Tried different tips and they still hurt my ears after an hour or so. Also once I bought the other two pair and compared sound, these were the worst of the 3 sound-wise imo.
Next up I bought the Jabra Elite 7 Pros. I looked at the Jabra Elite 75t but these were rated better and there is actually a newer version of those, the 85t, and the 7 Pros were rated better than even those and supposed to be more comfortable. Verdict is more comfortable than the Sony buds by a lot. The sound was better but the bass was punchy. I don't know what the fuck I'm talking about but calling it punchy sounds like something someone who knows things would say. The stay in ear factor was worst of the 3 no matter what tips I tried, and I have a lot of different sized and types of tips.
Jabra Elite 7 Pro in Ear Bluetooth Earbuds - Adjustable Active Noise Cancellation True Wireless Buds in a Compact Design MultiSensor Voice Technology for Clear Calls - Titanium Black https://a.co/d/5Q6YSOK
The final pair and clear winner to me were the Beats Fit Pros. Again I'm coming from some Powerboats Pros and these had a lot of the features I liked about the Powerbeats but large improvement in sound quality, form factor (oops I did it again) and fit. The bass was booming on these. Like it literally vibrates in your ear on the really deep notes. Impressive. They have a little wing that goes into your ear canal to help keep them in plant yet they are quite a bit smaller than the above two pair. The biggest downside is probably that the case is bulky compared to the other two. It's still less then half the size of the Powerbeats case. The "large" tips it came with fit pretty well and were comfortable but playing around with the alternate tips I had I was able to find a set that i liked a little better. Maybe the best thing about these is they have a clickable button on the right bud that actually works and makes sense. It's nice to be able to feel that you're physically pressing a button to pause/whatever and double press to advance to next song. The other buds I tried had sensors that were hit and miss.
Beats Fit Pro – True Wireless Noise Cancelling Earbuds – Apple H1 Headphone Chip, Compatible with Apple & Android, Class 1 Bluetooth®, Built-in Microphone, 6 Hours of Listening Time – Sage Gray https://a.co/d/eyPdJFB
I have an ok job but Wirecutter, if you're reading this, I'm willing to take on side hustles.