I used a Nano 5th gen, the last to have a clickwheel, until 2019. It was primarily for use at the gym but because I mostly listened to podcasts and didn't want to try to keep everything synced with Mac, Nano, and iPhone, it was the only thing I used for portable audio.

I've switched to using an Apple Watch to have wireless headphones but it's not great; syncing to the Watch's storage (I don't want my phone on me at the gym) is slow and the Podcast app can be wonky. Just today it stopped playing an episode in the middle for no apparent reason and I couldn't get it to start again. Some of this may be because it's a Series 1 Watch but newer models seem too expensive for possibly not that much better an experience.