If you use Outlook 2010 or newer, you can sync calendar and contacts with Outlook.com. To set up the account in Outlook, follow these steps. To add the account to your smartphone, choose Outlook.com or Exchange account type and enter your Outlook.com address and password.
Outlook 2003 and Outlook 2007 (as of October 31 2017) can only connect to Outlook.com using POP3 or IMAP protocols, neither of which sync calendar and contacts.
If you don’t have an Outlook.com account (or Microsoft Account), go to Outlook.com and create an Outlook.com account.
If you have a Microsoft account, you don't need to create a new account. If it does not have an Outlook.com email address associated with it, add an "Outlook.com alias" to the account. You'll need to use the Outlook.com address to set up the account in Outlook.
Add Outlook.com Account to Outlook
In Outlook 2010 or Outlook 2013, the dialog looks like this. Because it's going to be setup as an Exchange account, you can leave the name and password fields empty. Outlook will ask for the password after it finds the account.
After adding the account, the Outlook.com data file will be set as default data file but the default email account won't be changed. If you want to confirm these settings, go to File, Account settings (#2 in the first screenshot) to open the email settings dialog to verify.
If you're using Outlook 2016, you won't be required to restart Outlook after adding the Outlook.com account but you will need to restart it before changing the Address book. Restarting Outlook is required if you are using Outlook 2013 or Outlook 2010.
After the account is added...
In Outlook 2013 and Outlook 2016, you can drag the set of email folders to the top of the Navigation pane.
If you have appointments, contacts, tasks, or notes in another data file, move them to the Outlook.com folders. Open the folder, Select All (Ctrl+A) then use the Move to folder command to move the items. In the Calendar, first switch to a list view then select all and move. If you aren't sure how to do this, see "Merging Two Calendar Folders" for more details.
If your email account is an IMAP account and there are folders in it's data file named Calendar (this computer only) or Contacts (this computer only), make sure all of the 'this computer only' folders (including Tasks and Notes) in the data file are empty then right click on the folder and choose Open File Location. This will open File Explorer with the account's data file selected. Close Outlook and delete the data file. Outlook will rebuild it without the ‘this computer only folders’.