I had the same question and found the following hack for those without access to Xcode (which would allow attaching icons to playgrounds, I assume). Here is how I did it after some investigation in one of the sample playgrounds:
Close playground in question in SP4
Find playground folder on iCloud
CD into and further down into Contents
Create folder PrivateResources
Copy your image into new folder
Back in Contents edit Manifest.plist
Add XML lines to top-level <dict> :
<key>ImageReference</key>
<string><your image file name></string>
Open playground in question and edit (!). I found editing crucial as the icon didn't appear after just opened/ closed the playground without at least a minor edit.
I did it all on my iPad using Textastic for folder creation, file copying, and editing.
Topic:
Developer Tools & Services
SubTopic:
Swift Playground
Tags: