I can only give you examples from my thoughts when I was faced with this dilemma and what I did about it.

Simply: wired headphones don’t need to be charged. Having “true wireless” (aka airpod style) headphones, you need to stop listening to charge your headphones, which seems unnecessary to me, and I’m worried it would happen at inopportune times; I’m pretty bad with keeping things consistently charged, I usually charge them, toss them in a bag then promptly forget about them for a few months until I need them, and with some stuff, that means it’s dead by the time I pick it up again. Not a problem with wired headphones.

My car also is pretty old, not tape deck old, but the Bluetooth in the car is still Bluetooth 2.0, which isn’t the most energy efficient.

So when I got a phone with no headphone jack, I set out to solve a few things. Among those things: if it’s wireless, I need to be able to charge while listening, and output to my car’s aux, and an unpowered/wired headphone.

My solution to the dilemma came in the form of a device from Fiio, the BTR5. Basically the BTR5 is a Bluetooth headphone jack. It just connects over bt and outputs to a 3.5 (or 2.5 balanced) jack. It charges by USB C, and can charge while listening and it’s actually designed to do that. It has a “car mode” that will turn on/off the device depending on whether it is receiving power or not, so it will come on when you turn on your car by hooking it up to your vehicle semi permanently.

Now, I can charge my phone, and my BTR5 while I’m listening, giving me practically infinite use time. I have a small collection of IEMs that I can toss in a bag and it doesn’t matter if my BTR5 is dead or not, since I can charge it with my battery bank that holds a charge longer than other battery powered things I have.

On top of that, the BTR5 can also playback via USB. Aside from that, I also picked up a USB C charge/listen dongle as a backup and that works with my IEMs, or any other 3.5mm headphone or aux connection.

I also have a direct USB C to headphone adapter that came with one of my smartphones. Between all of my options I have never needed to make any compromises on when I listen to music or how I want to listen.

I also have some fully Bluetooth headsets, my favorite is from trekz, which mainly makes bone conduction headsets; i mainly only use that one headset but I do have others that I don’t pick up very often.

I find that most consumer Bluetooth headsets cannot be charged while in use. Even if you can physically plug in the charger while wearing them so it should be able to do both, I usually find that they will turn themselves off while charging. The trekz are not immune to this. I like them mainly for the bone conduction, but because of their inability to charge while in use, I tend to put them on the charger the night before I plan to use them.

I just throw my BTR5 in my bag with a few sets of IEMs, and my USB to headphone adapters. I have my power bank in my bag all the time as well (along with a USB C charger, which powers/charges my phone, laptop, power bank, BTR5, etc).

I don’t know what other people’s requirements are, but I found my solution. I won’t throw any shade at anyone who has different requirements, nor uses their tech differently. My solution isn’t your solution. I’m happy with my setup, and it works really well for me. I can put in my IEMs, wire up my BTR5 and listen as long as I like, when the BTR runs low on batteries I can stuff my battery bank in my pocket and plug it in to charge and have no interruption in my listening. I can also just plug the BTR5 into my computer by USB C and it will connect as an audio device over USB C and I can get my computer audio over my headphones without needing to unplug them.

I hope that fills in some gaps for you, I’m certain my use is not the only use cases that require a 3.5mm jack, and I know I have more significant demands than most (otherwise airpods wouldn’t be popular). So I know I’m in a minority, and that’s fine.

Let me know if you have any questions, or comments. Take care.