Let me start with that, if you have iTunes already installed and you are lost, because it is too complicated there is another easiest solution to manage your IPod with Winamp.
If that is the case directly proceed with Uploading files to my iPod using Winamp

Otherwise if you want to install iTunes, this tutorial will explain how this can be done.

Download iTunes from:

http://www.apple.com/itunes/download/

Start the iTunesSetup.exe file.

The first screen will be iTunes + QuickTime

It is strange that “you need one book to read another”, but as from Apple said: “It is important to install QuickTime which is required for important iTunes features.

When you click the ‘Next’ button the installation will proceed with Software License Agreement.

Read it if you like and check “I accept the terms in the license agreement” then click on ‘Next’ to proceed with iTunes installation.

The next screen is ‘Installation Options’ where you can choose what will be the default language for iTunes and the destination folder for the installation.

Also there you can remove ‘Use iTunes as the default player for audio files’ if you do not want that.
Personally I use Winamp and I do not want any audio file extensions to be associated with another player.

Click ‘Install’ and wait until it finish.

Start iTunes from the new icon on your Desktop and you will see again iTunes Software License Agreement.

Read APPLE INC. SLA for iTunes it and click ‘Agree’.

Welcome to iTunes pane has no interaction needed, so just proceed.

Find Music Files will ask you whether you want iTunes to search your ‘My Music’ folder and add files to the iTunes Library.

If you keep music files there leave both checks and click ‘Next’

Keep iTunes Music Folder Organized will be useful for you if you are not good with Windows file management.
I prefer to organize my music by myself.

When you make your choice click ‘Next’

The last page gives you a tip how you can Download Album Artwork with iTunes.
This requires ‘iTunes Store’ account and you need to go to the iTunes Store and create a new account , and then to choose “Get Album Artwork” from the Advanced menu.

Certainly this can be done only after you click ‘Finish’

Choose your country and sign up.

Happy iTunes usage!