Let's first make sure Outlook sync is turned on in iCloud. On you phone, go to Settings - iCloud and make sure Calendar setting is turned on. Then on you PC, open iCloud Control Panel (search for it if you don't see it, iCloud should be running in the background) and make sure outlook sync is checked.
Then restart your phone and give it a little bit of time to see if it works. Let us know what happens.
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