
Apple
AirPod Pro Series
Apple-integrated, great ANC, but fit issues & poor Windows support.

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Sennheiser Momentum True Wireless 1. They sounded the best of any earbud I have ever tried, ever, and the fit is perfect. I have tried many - Technics AZ80, DenonPerl Pro, Bose Ultra Open, Bose Quietcomfort, AirPods Pro, Sennheiser MTW3, Jabra Elite 10, Jaybird Vista, and others. None were better than what I already have, the MTW1. It’s a real shame that the later generations of MTW were not nearly as good sounding to me as the gen 1. It sucks because my MTW1 battery only last about 30 min these days, but I still use them when I want to really “listen”, because the sound quality can’t be beat. I would buy them again in a heartbeat if I could find another pair with a battery that was guaranteed fresh.
In the spirit of stopped production: Jaybird Vista. Noise canceling, although they are in-ear, I've ran mine in the wash many times and they still work, although after more than 5years, I feel their end will be near. I'm bummed, there is no other sound like theirs.
Have you looked at models with different size/material tips, behind the ear hooks, or hell - just go over the head with a headband. I am definitely very sensitive to earbuds fitting properly and a lot of popular models just don't work for me. BUT - I have been very happy with my Jaybird Vista earbuds for years now. I run with them regularly and have no issues. Also very satisfied with their audio quality. For the quality and user experience I get out of them - think I paid ~$100. Not the cheapest headphones in the world, but also far from expensive and I would consider an excellent value.
Maybe add Jaybird vistas to your list. I wear them hiking and at the gym. Plenty of bass.
Jaybird Vista. Don’t sell them new any longer but you may be able to find them still. Mine are 6 years old and still going strong.
Jaybird Vista. Had them for 3 years now

Apple
AirPod Pro Series
Apple-integrated, great ANC, but fit issues & poor Windows support.

OnePlus
Buds 4
Budget ANC king, but no wireless charging & windy transparency fails.

Beats (Apple)
Fit Pro
Workout secure, Apple-friendly, but wing-tips tear and case feels cheap.

Anker Soundcore
Sport X20
Value workout buds, secure fit, but connectivity can be iffy.

EarFun
Air Pro 4
Budget champ with great sound/ANC, but transparency has static.

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Technics - EAH-AZ100

Ranked #1
Beats (Apple) - Fit Pro

Ranked #1
ISOtunes - PRO Aware 2.0

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Shokz - OpenFit Series