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PGP

To use PGP, go get the freeware version from PGP Corporation, or if you don't qualify or want more features, buy the desktop commercial version.
The best combination, IMHO, is using Thunderbird as email client, GnuPG for the crypto and Enigmail to bind the two together. You can use your old PGP keys, if you have those, or create new ones.
What you should do breaks down into three steps:

Get Thunderbird from Mozilla
Get GnuPG and install it
Get Enigmail and install it

Now, the interesting thing is that the above three steps are equally valid for Windows as for Linux or Mac OSX! It may look intimidating, but the truth is that these three products install without any problems and you don't need to answer any weird questions along the way. The only little "trick" you should know is that the Enigmail file is an "extension" for Thunderbird, so you should save it to your desktop (for instance), then open Thunderbird, go to "Tools" -> "Extensions" -> "Install" and select that file. Otherwise, it's all downhill, actually.

Get my public key, which is available as file and looks as follows:

The "fingerprint" for this key is: C18A F357 D8AA E4D1 C334 D4FD 32CB 5D56 C7D5 6E11

This key is also available from http://pgpkeys.mit.edu:11371 and ldap://certserver.pgp.com, both of which are automatically used by PGPKeys, a utility included in the PGP desktop.

Once you've set up PGP Desktop or GnuPG/Enigmail and loaded my key, you can write encrypted emails to me and verify my signature on email or files I send to you. For me to send you encrypted email, I have to know your public key, though.

A tip: when sending encrypted email, encrypt it both for the destinee and for yourself. That way you can actually read your own sent emails later...

Using PGP with Outlook Express

The freeware version of PGP doesn't support Outlook Express directly. Older versions do, but not very well. This is so easy to work around that it is not a reason in itself to go and pay for something or for not using PGP. The way to do encryption is:

Write a new message in Outlook Express
Hit ctrl-A, which makes Outlook Express select the entire contents of the message
Hit ctrl-shift-E, the hotkey for PGP to do encryption
Select the destinees key and also select your own key (so you can decrypt and read sent messages later), click OK
Automagically, PGP has replaced your plaintext message with the encrypted version, so just send it.

To decrypt a message you received:

Open the message in Outlook Express and click somewhere in the message pane.
Hit ctrl-A, selecting the entire encrypted content.
Hit ctrl-shift-D, the hotkey for PGP to do decryption
Enter your personal passphrase to enable decryption
Automagically, PGP pops up a window showing the decrypted contents, but it does not replace the original encrypted message. If you want to keep the decrypted contents to quote in a reply, for instance, you have to copy it from this popup window.

Honestly and truly, this is all there is to it.

Using PGP with anything else

In whatever textbased program, you can select the text to encrypt (or decrypt), then use the PGP hotkeys, which by default are ctrl-shift-E resp. ctrl-shift-D.

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