LinkBuds (WF-L900)

I've had samsung buds pro once, but they never sat well in my ears. And that is important. Then I bought sony linkbuds s, they were amazing. Sat very firm in the ear, great noise cancelling. But one of the batteries got bad after only a year, lastes only 5 min. Now i have nothing ear 2, pretty good budget in ears. The noise cancelling isn't that great, but they sit very firm in the ear and have lasted 2.5 years now.

I use a Linkbuds S. Feels special to me keeping it Sony branded and amazing to have ANC and quality sound while gaming on PSP.

They’re older, but the most comfortable wireless earbuds I’ve encountered are the Sony Linkbuds S. The main reason I bought them was because I read so many comments about how comfortable they are compared to everything else out there, and it really is true. And the sound quality is very good as well.

Just my 5 cents : I have the Sony Linkbuds S and they are really underrated. Small, fit extremely well in the ear, good sound and fair enough noise cancelling. Also, the bud part is full silicone, which make them very comfortable. If you have small ear that tend to not agree with earbuds, go for a try,

Jabra elite 7 active or sony link buds, both great mics and all rounder daily use.

Shokz open run pro for secure fit or sony linkbuds for better calls in open ear style.

I had no problem running with these: SONY Linkbuds S, JBL Live Beam 3 Not bad, but not good enough for me: Huawei Freebuds 5i, JBL Tune Flex

I don't think the Live Beam 3 go deep in the ear canal but they seal your ear very well to avoid movement, the Linkbuds S do go deeper.

As someone with similar struggles - soft in-ear hooks. There's the occasional unicorn design that just works, but your best bet is something that fits securely not just into your ear canal. Unfortunately most of that category is sports gear that's both very bassy and uncomfortable to outright painful for longer sessions, but something like the Sony Linkbuds, basic Beats Fit Pro or previous gen of Bose QuietComfort might pop up just within your budget if you keep an eye on sales and discounts.