This should be posted in THIS section.
However, I've not used Outlook since Mozilla raised its head and can't remember the slightest thing about it either!

You can just attach pictures to Outlook and it'll send them. Depends on your emails size limit for sending, which is usually 8-10MB per email.

If you'd like to "zip" them up to smaller sizes, you'll need to "compress" and then "archive". You can choose your compression ratios normally and the archiving can also be chosen, usually in ZIP format.

FilZip is an archive and compression tool. It can compress/decompress several files to or from a single file making sending over the net easier.

All you need to do if its installed is, rightclick the file/folder you want to archive > choose the format you want to archive and compress it in i..e TAR, ZIP, RAR and then archive it in a certain directory. After that you can just attach them all on as one file to your email

BTW do you have Filzip version 3.06?

Thats the latest anyway. You can download it here if you want: http://www.filzip.com/en/download.html

Thunderbird is a much better emailing product in all ways so maybe you would like to move to that instead.