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

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Like others said they were pioneers in the noise cancelling space but I actually got the bose sport run free (I think that's what they're called and I don't like noise cancelling I prefer to be aware of my surrounds when walking and jogging and even at work I like to keep an ear out). Got them almost purely for their stayhear tips. The tips have a funny wing design that have a good hold for jogging they stay in place really well and i find them really comfy I even wear them for hours at work. Sound quality is mediocre though haha.
I got bose sound sport for this reason keeps me aware out and about and also in the office I can turn in to people's convos still
Runner here. Previously used Bose Sound Sport Free earbuds (now discontinued) for years and loved them. Bought QC Ultra Gen 2 and really disappointed with them. Would not recommend. Very very expensive. When running and noise cancellation is on, you can gear the rubber parts if the ear buds bouncing, awful. You can now turn off noise cancellation thanks to lastest update, this really helped. If I was buying again I would buy the standard Quiet Comfort earbud. Looks like the old Sound Sport earbuds that I had. I tried them in an airport and liked them. Much more cost effective and I suspect better for running. Please report back with what you buy and your experience using them!
Fellow large-ear animal, Larger outer ears, and large ear canal holes (both depth & diameter). Without wings or hooks - the vast majority of earbuds that rely on eartip-friction for retention - fall out of my ears, or don't seal. Even with larger tips. 95% of what you listed in your post is in my Google Docs notes - made me double-take (for same reasons). I've got all size and dimensions of every Spinfit, Sednafit, and a long list of Japanese and Chinese tips all extracted into tables for quick cross-reference for fitting. (sometimes I have to change summer/winter tips due to extreme weather in PNW mountains and using outside much of the time. Extreme cold mountain air, and moisture, changes tip fit and maybe ear canal size just enough to cause fit issues....) Some copypasta from my notes: 1. Sony Linkbuds S - Overall - one of the all time best for fit. Fantastic w/the right tips, but they're also extremely light and "meh" at best for complex music. Best phone call/mic & ANC earbuds I have owned, until Sony fried them w/the infamous firmware update and refused to replace mine. X4s were good and waiting to test 5's cheaply, when the 6's come out next spring. 2. Anker Soundcore Liberty 3 Pros - all time favorite wireless/BT TWS earbuds, factoring in app w/DSP & ANC tuning. Full IEM profile nozzle so run wide/long Spinfits most of the time. Right on the edge of the Nothing Ear volume-step issue, but thankfully the active DSP/ANC app allows for infinite tuning of DB levels per "step". Mic & call quality mediocre to poor. Have to "jiggle" them a lot to get them in place properly, and repeat on long walks/hikes. 3. Soundcore Sport X20s - hook-retention is great. The X20 tips do work-loose from my ear hole regularly, when moving around. Even just walking the dogs. Constantly push them back in, to restore seal and bass (and listen to the mics squeal). Tricky to find a tip large & deep enough for the tiny TWS-style mount, as you know. If you don't care about bass or ANC - the largest X20 tip is fine, IMHO. Mics and call quality are excellent for the price-point. Audio is okay-ish. Liveable but not desirable (said with older, suboptimal hearing). Doesn't have L3P volume-step issue. 4. Samsung Galaxy Buds Pro/Pro 2s - can make them to fit with the right tips. Buds Pro, w/Comply I could sacrifice a bit of sound quality, and use them all day moving around just fine. Buds 2, much better call quality and ANC (2nd to Sony). But due to extremely short TWS nozzle could only get them to fit with those huge, sticky Sednafit Xclear tips. Great at a desk. If I move around a lot, the Pro 2s will fall out. Even w/large sticky tip: the tip stays in my ear, but the earbud comes off the tip and falls. 5. Bose: had a TWS model with ear hooks and large tips I liked for calls (equal to Sony). Decent for music, better than X20s or Galaxy Buds Pro. Unfortunately they caused me ear pain, and gave me a splitting headache, even after weeks of attempting to get used to them. Had to return them. Only earbud/IEM product I've ever had a physical pain issue with (out of 100s) and I rarely ever get headaches. Also, IMHSO (humble, subjective opinion) using old, suboptimal ears: Bose audio/music quality is just not worth the price - not for what I listen to. 6. I've read the mid-range Meze fits larger ears well, but no option to try them out where I am and well past my "experiment" price. (I like Meze cans.) 7. Wired: If Wired is No-Go for your, skip this section and go down to "No-Gos"
7. Wired IEMs/Earbuds: My favorite in-ear audio products are all wired, w/exception of L3Ps. Obviously the wide range of ear-hook cables, earhooks, and eartips enables mitigation or remediation of most large-ear challenges. My most-used IEM models are from BQEYZ, CCA, Sennheiser, 7hz, Truthear (and cans). Favorites, with random, super-subjective personal takes: Truthear IEMs: overall best bang for the buck. OG Blue/Reds, Hexa, Gates. Most-used for travel. Efficient, easy to drive, no crying if lost. Mainly use their OEM tips. They fit great, feel great, sound great, at budget price. People say mics are good on calls, but rarely use. So not much data. BQEYZ Winter/Winter Ultra: slightly larger than most of my Truthears. Much more expensive. Still efficient. Fit perfectly. Have some kind of magic for certain types of stringed music - any acoustic/classic strings, up to aggressive jazz (John Zorn/Book of Angels - Lucifer) and prog rock. Nice tips - wide range of diameters and thickness - but OEM tips too shallow. I go back and forth between deep Final Audio (best except bass) and Spinfits (bass) for BQEYZ. Not technical (for their price point) but Winter series is one of the most "forgot about everything for 30 minutes while gooving to music" IEMs I've ever owned, esp adding DSP. CCA Hydros - all around current favorite IEM. Great long/deep XL OEM tips. IEM shells are metal, clanky, and not sure how durable, so stay on my desk. CCA C12s lighter, for walking about, but don't come close to Hydros for audio performance. Prefer Truthear models to C12s. But if I could keep "only one IEM/Earbud for everything": CCA Hydros. Ridiculously technical and well-tuned for $120 (avg sale price), great for almost every music genre, Dolby Atmos, games, etc.
2025-12 update to wired list: AFUL Explorers: the largest of the longer, blue inner-nozzle & black outside, OEM tips - fit great. IEMs are very light, efficient, well-rounded. Great daily drivers and might do well with a Mic cable. (I use Truthear Gate for wired calls now but Explorer much better sounding to me). The Explorers remind me a lot of the BQEYZ Winter IEMs, but with additional BA-driver clarity up top. Amazing $90 sale price IEMs. The one risk I see for them w/large ears: the nozzle has no lip so if your ear canal size requires a wide, sticky tip (e.g.-Senafit or foam) which often run shorter - I can totally see these pulling off the nozzle. (vs. IEMs with a large retention lip-ring at the end of the nozzle.) But using their long OEM tips, they are so light - zero issues. My Go-To Dog-Walking/DogJog IEM now.
I’m in the marking for a new pair of wireless earbuds that aren’t gonna crap out on me. For reference, I’ve had the apple AirPods Pro 2nd Gen and the Bose Soundsport. The AirPods are the most fragile earbuds I’ve ever used, I like to think I’m quite careful when it comes to earbuds but it didn’t take long for them to stop working after a couple falls to the floor or a splash of water or sweat got on them. They also had very harsh treble to my ears. The Bose’s battery just wasn’t up the standard and wore out very quickly, also wouldn’t charge fast or well. I’m looking for good sound quality, something that won’t hurt my ears after long periods, and won’t break or wear out quickly. I’m not exactly enthusiastic about dropping $400 on a pear of earbuds, but if I know they will last a long time then I’ll consider it.
I upgraded from Bose Soundsports to the Ultra Open (bone conducting) when my Sports died. I wish they were a hair louder, but otherwise very pleased.
Hi there - I was a Bose Soundsport + QuietComfort Fan for a while - both started crackling after a few years of use. Then this sub turned me onto the Sennheiser Momentum True Wireless 2 and purchased a pair in April 2023. Loved them but they died in less than a year... I complained and they sent me a brand new (or maybe refurbished idk) Momentum 3. Those died in about two years (one ear bud stopped charging) and purchased the Sennheiser CX True Wireless as a "lower cost" option in Jan 2024... it is now Apr 2026 and one Earbud is just refusing to connect, but is "on". Did a factory reset, etc. I am now scared to buy For my needs, I don't really care about the best quality sound (I mean, not potato quality) or noise cancelling. I ride the subway, plug these in at work, and workout with them. I just need something that won't die in 2 years and maybe holds a 6-8+ hour charge. I'm kind of sick of shelling out money every couple years and just having them poop out. To be fair, I am okay with spending more money but I want to be sure that these will at least give me 3 years of use and get me through a long haul plane ride. I *would* buy headphones but I dont like sweating/working out with literal earmuffs and for me, they are nice-to-haves not need-to-haves. EDIT: I purchased the EarFun AirPro 4 (not plus) to hold me over and I love them. (Even though my bf said he will buy me a pair of Sony). Perfect for my needs, not a super distracting ANC, good sound for gym/commuting def not as warm as Sennheiser but as a non-audiophile, this works, and only $60 bucks so if they die in 2 years, I wont be too eaten up about it. I'll likely upgrade to the 4+ once these die to see how I feel about it.

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

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Technics - EAH-AZ100

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Beats (Apple) - Fit Pro

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ISOtunes - PRO Aware 2.0

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Apple - AirPod Pro Series

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Shokz - OpenFit Series