Very happy with one Sennheiser CX True Wireless bud for most of my rides. Pretty bombproof too, have dropped mine a number of times.
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I use a single Beats Studio Bud to listen to things while riding. Iāve done the pair in transparency mode but it reduces the spatial awareness that the earās own acoustics provide to hear things coming from behind. So itās usually the right bud (due to left-hand drive cars and having to ride toward the right-hand-side of the lane), no noise cancellation or transparency. Battery life is great and the things donāt fall out.
I tried the same with my Jabra Elite Active 75t earbuds but they arenāt as stable in the ear and could jostle out on rougher terrain or when I really sweat profusely (itās DC, we have legit ugly humidity in the summer). Iād rather not worry.
Tried Shokz. They wereā¦ OK. But you often end up sharing your music or podcast with others riding alongside. Audio quality is also wanting, even on the latest ones.
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I must ride far more slowly than you because Iāve had good luck with Shokz. Edit to add that I am very slow, so this might be the reason.
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Airpods Pro here. And I bought replacement aftermarket silicon tips and theyāve been great. Would (will) buy again.
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Iāve been using the Moondrop Pill because nothing will stay in my left ear
Plenty of spatial awareness and theyāre good for music or podcasts, relatively cheap too
Iāve been using the right earbud if Anker Soundcore A40 for about three years, 6-8 hours per day overall. Love them. I replace them about once every four to five months when I lose a bud or step on them or something and theyāre cheap enough that I donāt mind.
Might not be what youāre after but I use really cheap wired headphones (Panasonic ones that are about Ā£4 a pair on eBay) and then plug them into a little bluetooth receiver (a previous iteration of Fiio Btr11 which is ~Ā£30). I donāt really like the wireless buds that lodge into the ear canal, and I think the cheap old fashioned buds stick out less and let the road noise through better. Also no worries about them popping out in traffic.
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Well donāt sell yourself shortā¦thereās several models of Shokz, and most importantly (like the descriptions of earbuds fit above), Iām sure the bone-conducting tech works better on some than others.
Youāre not an idiot for doing that. Deaf cyclists are allowed on the road so even with one earbud in you will hear more from your surroundings than a deaf person will.
I use a cheap pair of earbuds from Amazon, Ā£15-Ā£20 for them and they hook over my left ear so hopefully it wonāt fall out so easily. I donāt use noise cancelling, just want some music or a podcast to listen to while out and about.
So far no issues, they stay in place and last long enough for a 6hr ride. More often than not itās a lack of mobile phone signal which curtails my in ear entertainment when a podcast Iāve not downloaded prior to the ride stops playing.
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More airpods pro. Mostly because they are good enough for purpose, and I already owned them for work calls. One less thing to carry, lose and / or forget to charge. Occasionally, one is knocked out of an ear by helmet removal (caught on strap, usually). Wind noise is bad enough that conducting a call while moving is impractical ā but works well enough for emergencies that the limitation is tolerable. Iām not sure how much the āstemā or āstalkā of the earbud jutting out so far contributes to the wind noise, and suspect it does, but have not cared enough to test other shapes (maybe when they finally die).
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Iāve tried a bunch (I have a lot of headphones).
Initially used wired Apple headphones (theyāre cheap), however not durable enough for rain/sweat. Also very visible. Even if youāre minding your business in a bike lane or trail, I found people still wanted to share their opinion with me about headphones as I had a big white cable dangling out of my ears.
Then I tried some Sony WF-1000, but found they just didnāt stay in very well, and also picked up a lot of wind noise. Then moved onto AirPods Proās, which are great as all the controls are on the AirPods. I personally found these either too separated from the real world with noise cancelling enabled, or simply too much external noise in adaptive mode.
More recently Iāve moved to the Shokz Openrun Pro2, and despite the controls being a bit fiddly, I really like the fit (I put them on last over my helmet). The sound is fine (way better than the earlier models) although itās worth tinkering with the EQ settings depending on what youāre listening to.
So far these have been the best overall experience for me taking into account sound/fit/external noise/etc.
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I too use buds every time I ride alone. I have had good luck with inexpensive Soundcore buds. I have found that noise canceling buds donāt work well while cycling due to the air movement around the microphone of the bud. Getting the right silicone ear cushions is the key to good sound quality and low noise.
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Long time AirPods Pro user, the new AirPods Pro 3 are excellent.
I put a shortcut on my iPhone/Watch action buttons that pauses the music and turns transparency mode on.
Iām experimenting with the Oakley Meta glasses as headphones. Theyāre better than I expected but you need to have them at nearly full volume.
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I use these same ones. Through rain, intervals, everything for hours and hours of riding theyāre great. Especially for the price. And I agree they donāt need ANC. They block out enough wind that itās not an issue at all. The only time Iāve had them fall out is when I take off a neck buff or something. Iāve never ever had them fall out on their own.
Iāve been using Jabra elite 8 earbuds (well, one in my right ear) for years, and itās brilliant.
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I hate you all for having ears that airpods stay in!
I want to use them because they have hearing aid functionality and noise cancelling ability at a much lower cost than my hearing aids.
I have some and have tried various ear hooks to hold them in, but they still come out.
My solution is $8k worth of hearing aids, which have infuriating noise reduction - when the wind noise builds up they turn down their sound output instead of just the microphone volume. 
I moved to Shokz, too, after having single earbuds fall out mid ride, bouncing down the highway. In winter, when I have a skullcap that covers my ear I will use a single earbud that canāt fall out. The sound with Shokz is very good except when a noisy truck or bus passes me during my commute.
I realize the question is specific to earbuds/variations. But wanted to say that for several years I had great luck with Shok (sp?) OpenRun models. Previously I was a right side only listener for traffic. With the out of ear transmission, I could literally hear every pebble on the road. I was also just starting to have some minor hearing loss, and it was amazing how much better I could hear overall when not transmitting through the ear canal. More recently, Iāve switched to hearing aids because I wear them all of the time in general. They also let the outside road sounds in.
The new AirPods Pro 3 have very different rubber(?) tips than the v1/2 models. They are much firmer, and as a result really grip the inside of the ear better. They also come with 5 tip sizes so each person can really customize. Give them a shot.
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I only use shokz on the bike, but I also only listen to music and they are great for that. Used to do the one earbud thing, but all that did was make it so I couldnāt really hear the music and couldnāt really hear the traffic. Shokz allow me to have music, but still talk to people and hear traffic and whatās happening around me.