I've always run with an iPod Shuffle, but that's more because I like the physical buttons. That said, I've been thinking of going cordless with bluetooth headphones paired to either an AW or and iPod Nano. I've heard some reports of poor bluetooth connection when using an iPod Nano. But syncing song is pretty fast, although you have to physically connect to your Mac. The Apple Watch on the other hand will allow you to run without an iPhone, but the time to download and synching songs/playlists is rather lengthy. Any experiences with either would be appreciated.