I only use wireless headphones and have for a very long time. I own more than I care to admit. My current perfect grouping are:
For the gym I use the JayBird Runs. They dont fall out, block out the horrible gym music and sound great.
For bed I use the Beats X. They stay flat in your ears and dont hurt if you lay on your side.
For the majority of my listening I use the AirPods. Best pairing and great for calls. I wear them one AirPod at a time so in theory I have unlimited listening since one AirPod is always charging. I used to wear them in the gym and they never fell out either, but they dont isolate the noise enough so the crappy gym music was always bleeding in. However when I am out on my bike or running I love the AirPods specifically because of that