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

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Soundpeats pearl clip pro would be my recommendation for under $100 - less than $50 actually.
I have the Pearl Clip Pro and the Pop Clip. The Pearl is a really good clip style bud. The sound is full with decent bass and it works well for calls. The Pop is only better in that it has a physical button control and is slightly more comfortable. I recommend the Pearl.
The Bose are great for low volume high quality music. If you don’t want to pay that much the Soundcore Aerofit 2 is my next choice, followed by the Soundpeats Pearl clip, the Earfun Openjump, the Tozo O2 and, the cheapest option, the Soundpeats Breezy.
The Bose ultra open is my favorite low volume listening experience and its immersive sound mode is superior to all other spatial type settings. Its only weaknesses are call quality and maybe battery life. I bought mine refurbished for $190 so take that into account. The Pearl Clip and the Soundcore Aerofit 2 are very close in sound quality. The Earfun Openjump is the most comfortable with a very long battery life. Whichever one you buy, you will probably be pleased with.
In the US you could get the Soundcore Aerofit 2 around $80. For an open, it has good bass and is one of the better open hook style earbuds. Or look at the Earfun clip for around $50. For a clip, the Earfun Clip or the Soundpeats Pearl Clip Pro are pretty good for around or under $50. Even cheaper, the Baseus BC1 has decent bass. I own all of those so feel free to ask for more information.
I always have my Bose open ultra to fall back on and the cheapo Haylou Airfree for ‘can get wet and die’
The AeroClips. More comfortable than the Bose (but those sound a bit better). Also got the Soundpeats Pearlclips, because I found them for like $18, not bad, surprisingly good for side sleeping.
The pearlclip pro are high on my list )also coz I see them here for $20 refurb)
Does anyone know the price point of these? I got an email from SoundPeats for 35% off and says I can save $52… That seems like a pretty high amount for SoundPeats. I’ve had the TrueEngine 3 SE, Air3 Deluxe, PopClip and PearlClip Pro and will still probably get these if they’re $150 but was just curious.
The ones I have are SoundPeats as well but the Paperclip Pro model, and I feel like the sound doesn't go directly into my ear since the speakers are a bit to the side. Doesn't seem to be the case with the model you sent though, do you find them comfortable?
I got some soundpeats pearlclips for around $35 from aliexpress. Check for coupons.
The Pearlclips are comfortable. Look a bit like earrings, do not block any outdoor sound and are well reviewed for clip on under $50. Jlab Opensport are $20 at bestbuy. (Overear) Baseus BC1 openear is another clip that you can get for $20 at amazon.
I considered the PearlClips but at $79.99 CAD they're more money than I wanted to spend right now even with the online coupon, sadly. Those, the Soundcore AeroClips, or absolutely ideally the Bose Ultra Opens are going to be a future purchase, like on Prime Days or the Black Friday sales if the cheaper ones work well enough for my current purposes. Thank you for mentioning them, though!
Update! I went to AliExpress like you mentioned and got a pair of PearlClips Pro with the first-time buyer coupon for $40 CAD! I didn’t think of looking there so thank you so much!!
They’re really good! Positioning on the ear is critical but the result is worth it, even if it annoys the crap out of my mid-upper piercings getting settled but once positioned the sound quality is more than just acceptable. Now keep in mind I’m comparing them to my Sony XM5s, Beats Fit Pros and AirPods Pro and while they don’t quite have the robust bass those have, the bass in the PearlClips is pretty decent. I absolutely recommend them to anyone.

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