I have some of the Sony link buds fit for casual work listening, they are the most comfortable I’ve come across and I’ve never had them fall out of my ears, which has been an issue for me with other designs. They are probably a little over your budget but also on sale often enough. Sound is as good as one would expect for wireless earbuds. They have all the sorts of features modern buds seem to have. But yeah comfort and not falling out are my priorities with a Bluetooth set after the basic does it sound reasonably good.
I have a pair of Tozo NC9 wireless buds I’ve been using for a year now. I honestly expected them to be crap due to the Shenzen-type brand and price ($40). They’re shockingly good for the money. They won’t be impressing your audiophile buddy but the sound quality is perfectly good for listening to tunes and audiobooks at work, the noise cancelling is decent, and the fit is extremely comfortable and secure (once I figured out how to turn them correctly). Mic quality for phonecalls is quite good too (not sure if that’s a factor for you). Before these, I used the 5x more expensive Galaxy Buds Pro which had better noise cancelling but otherwise were not very impressive at all!
If very strong noise cancelling is your biggest concern and price is very flexible, I have heard rave reviews of Bose, I believe their noise canceling is still the best on the market. But I don’t have personal experience with them. I can just say Galaxy Buds Pro were very overpriced for the experience, while these Tozo are quite a good value.
They aren’t ANC, but they are designed to cut out a lot of external noise and succeed at that. They are what I prefer to listen when I’m flying.
If you must go wireless then avoid the terrible AirPods style design and get a set of Shokz OpenRun (or whichever Shokz best fits your budget) bone conduction headphones. Pair them with Etymotic earplugs and the results will be close to the ER2XR.