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

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I have the moondrop pill and the OnePlus buds 3 pro but I don't prefer one or the other in total but each has their use cases. I mainly love the clip on because they're comfortable and that's pretty much it, sitting in work calls for an hour or two and I found earbuds just get annoying and start to hurt but clip ons actually allow you to wear them the whole day and barely feel them.
I have a pair of Moondrop Pills. Pretty good. It's earclips so it stays on well. I usually put in low gain but when I travel outdoor I put it on high gain.
The moondrop pills are pretty good Edit: don't expect masses of bass though
Moondrop Pills are a solid choice.
I run with the moondrop pill. They clip onto my ear well, but I don't know if you have biggers ears than me or smthg.
Do you have a ranking of those you've tried? I have the Moondrop Pill, and I kinda do the same thing, as in wear them til the battery dies. Pill doesn't have any kind of decent battery to begin with, so I'm looking at other options. I know Jbl has a clip style coming out in a couple months too
Are you looking specifically for in ears? There are buds that have an ear hook, so they won't fall off, but it still requires a good seal to get proper audio from them. Have you considered open ear buds? They don't require any seal in ear to stay in place. They either have a hook over your ear or clip around the side. I honestly go for my Moondrop Pill over far more expensive in ears most days.
Hmm. There are several cuff shaped that fit within that budget, but none that I know of that fit your description for music. I have the Moondrop Pill. Some annoying quirks, but music is fine and its great for podcasts. I think there's an over ear open headphone from Jlab thats new as another option to look at.

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