The transition from Windows 3.11 to Windows 95 is the greatest leap in the Windows product line for me (including design).
I remember seeing the '95 start-up screen and its new UI for the first time - I was quite amazed by how much better it looked (I was at an impressionable age back then).
The Windows 95 logo always felt unsettling to me. At least part of it is because the main part of the logo curves downwards in a sad/frowning sort of way.
I remember seeing the '95 start-up screen and its new UI for the first time - I was quite amazed by how much better it looked (I was at an impressionable age back then).