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

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I wear Rayconc Essential Open,,they're over the earbuds and they don't hurt my ears
I've been using these [Raycon open earbuds](https://rayconglobal.com/collections/open-audio/products/essential-open-earbuds) for a couple months and find them very comfortable for long stretches of use.
Raycon just gave me their Open Ear Earbuds to try. They turned out to be great! I'll be using them for local running, where I have to hear if a car is coming. For trails or races, I use Skull Candy plug in over the ear headphones.
I had similar issues with Raycon's mic quality - it's pretty hit or miss tbh. The open earbuds are better for letting ambient sound in but I'd honestly look at the Shokz OpenRun instead, their mics are way more consistent for calls
raycon isn't really made for sleeping though, they're way too bulky. i use sleep earbuds on flights all time for work and regular earbuds just don't stay comfortable when you're trying to rest your head against window or anything. from the ones you listed, i'd probably go with ozlo since they're specifically designed for side sleeping. the noise masking works pretty well for airplane engines in my experience, though it's different than active cancellation. somnipods are decent too but battery life wasn't great when i tried them last year.
I had this same problem and Raycon is the only earbud that fits and stays put no matter what. I would try them out.

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