Getting outlook to work with Postfix can be a little tricky. I assume here that you are using some form of SASL authentication. Postfix supports SASL through a third party library, either Dovecot or Cyrus. When using SASL, the only authentication mechanism that Postfix supports is PLAIN. Obviously you don't want to submit this over an standard TCP connection, so it is best if you use something like TLS. Postfix will support TLS and SASL, using the standard port 25, not the higher SMTPS port. When you look at your logs you can verify that this is occurring because you will see ,TLS at the end of the connection.
If the above information does not help to get you working with Outlook, please provide some additional details regarding your configuration. Unfortunately, the only error message provided is vague in typical Microsoft fashion and amounts to that operation didn't work (duh!).
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