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When composing a message in Outlook, you should see a From box with a down arrow. Click the From box and (if you don't see the From address you want) click Other Email Address.... and choose the From address you want and the Send Using account. You can enter any From address you want. Of course, this may cause the reputation to suffer and a higher likelihood the message will be classified as spam due to the Envelope-From not matching the From header address.
If you don't see the down arrow in the From box while composing a message, click Options at the top and enable From in the Show Fields area.
You can also create a new Account in Outlook. This could contain any alias you have set up at Fastmail for that account. I would set up IMAP accounts rather than POP accounts.
Bill
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