PGP is pricey these days – starting at $83/yr, single quantity.
If you only need to encrypt files and e-mail in Windows, consider using GPG. It is compatible with PGP, and it’s free.
GPG has an Outlook plug-in, and tools to manage keys (including importing your PGP keys).
One thing GPG won’t do is create self-decrypting archives.
Get GPG here: