Several forums on internet are filled by question on how to configure Outlook2011 to be used from behind a company proxy server. Assuming that this traffic is not blocked by the proxy server itself, the setup is fairly easy.
To get Outlook 2011 for MAC working when you are connecting through a proxy server at for example your company. You should configure the System Preferences -> Network settings of your OS itself as Outlook 2011 uses these global OS parameters to connect.
To avoid any confusion , if you are connecting to a secure OWA setup using HTTPS. Configure the Secure Web Proxy ( HTTPS ) component, not the normal web proxy or Socks proxy as these are not used.This seems like a straight forward config, yet alot of confusion is read on different forms regarding this topic.