Aivar Annamaa added the comment:

In case this issue becomes active again, I'm listing my design implemented in 
Thonny IDE (http://thonny.org) -- see the attached png.

If you decide same design is suitable for IDLE, then I'm happy to create a 
version of the dialog without Thonny dependencies. Here's the current source: 
https://bitbucket.org/plas/thonny/src/master/thonny/plugins/pip_gui.py?at=master&fileviewer=file-view-default

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nosy: +Aivar.Annamaa
Added file: http://bugs.python.org/file46821/thonny_pip_gui.png

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<http://bugs.python.org/issue23551>
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