This program does what I believe you're after:
Alladin Systems ZipMagic
If it wasn't a memory hog it would be my favorite ZIP program I've used.
Some highlights from their details page (Note that its even cooler in Outlook than Outlook Express):
Quote:"Insert Zipped File" option for Outlook Express & Outlook
This unique feature allows you to zip a file at the same time you are attaching it to your email. A special checkbox appears at the bottom of the file attachment window. Once checked, the file is zipped while attaching to the email.
AutoZip for Outlook
The ZipMagic AutoZip feature automatically sends Outlook email attachments zipped without any additional effort. Simply attach the file to your email and as soon as you send it, the file zips.
Another useful feature of the program:
Quote:Use Zip Files without Unzipping Them First!
The magic behind ZipMagic is our patented ZipFolders® technology. It makes your compressed zip files look and act like regular Windows folders! So instead of launching a separate utility to see what's inside a zip file, just open it like any other Windows folder. And since ZipMagic unzips and zips invisibly in the background, you can open, modify, and save documents within zip files as if they were regular files. You can even run many programs from inside a zip file!