The original “Happy Mac” icon began to look a little dated, but it was loved by people who used the computers, so it was reinterpreted.
The square and the smiley face echo the face on the original icon. The lighter, human face in profile is a smiling person sitting in front of the screen, using the Mac.
Care to likewise interpret a very poorly rendered rainbow window flapping in the breeze?
My first experience with Microsoft was back with my Atari 800 with a version of Microsoft Basic in the early 1980s.