For starters, your music needs to be in Apple’s Music app on your iPhone before it can sync to Apple Watch. This includes songs added from Apple Music, purchased from iTunes, and even music you’ve added from other sources as long as it’s in the iPhone Music app. Music from third-party services like Spotify and Tidal won’t sync to Apple Watch yet.
Apple Watch can’t stream music over the Internet like iPhones so the music needs to be downloaded and synced like back in the iPod days. Apple Watch has a limit of 250 songs or 2 GB which you can change in the Watch app on iPhone under Music → Storage Limit. The Watch app on iPhone is also where you will set which music to sync. You can only sync one playlist at a time, however, so you may want to create a new playlist of music that you want to sync ahead of time.
Otherwise you can go to the Watch app on iPhone and find Music → Synced Music to select a playlist. My preference is to create a playlist called Apple Watch and add music to it specifically for syncing to Apple Watch. This is a workaround for the limitation of only being able to sync a single playlist and not multiple albums or playlists. You can create a new playlist from the Music app on iPhone by going to Library → Playlist → New Playlist where you can give your playlist a name like ‘Apple Watch’ (or WATCH) in my case) followed by an optional description, artwork, and public or private status. From here you can tap Add Music to pick songs and albums to add to your playlist.
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You can even pull from multiple existing playlists (just keep the song count or storage amount in mind). You can also add music to your playlist after you create it from your library when browsing songs, albums, and artists. Once your playlist is set, head back to the Watch app on iPhone and find Music → Synced Music to select your new playlist. You can update your playlist from your iPhone at any time to change your selection too. Just keep in mind that music won’t sync from iPhone to Apple Watch instantly.
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Syncing music from iPhone to Apple Watch happens over Wi-Fi when your Apple Watch is charging, and your selected playlist will need to download to your iPhone (which happens automatically after being selected) before it can sync the downloaded music to Apple Watch. If you don’t want to create you own playlist for Apple Watch, Apple Music members can optionally subscribe to playlists that have already been curated.