Yes there are two topics about control.
1. control whether we show the warning 
2. control whether we try to load win32console
This issue mainly targets `2`, so:

```rb
if Pry::Helpers::BaseHelpers.windows? && !Pry::Helpers::BaseHelpers.windows_ansi? && Pry.config.load_win32console
  begin
    require 'win32console'
    # The mswin and mingw versions of pry require win32console, so this should
    # only fail on jruby (where win32console doesn't work).
    # Instead we'll recommend ansicon, which does.
  rescue LoadError
    warn <<-WARNING
For a better Pry experience, please use ansicon: https://github.com/adoxa/ansicon
If you use an alternative to ansicon and don't want to see this warning, you can
add "Pry.config.show_ansicon_warning = false" to your .pryrc.
    WARNING
  end
end
```

If need option to switch showing the warnings, add another option(e.g. `Pry.config.show_warning`).