I would like to be able to push my work calendar items up to an Outlook.com account. There are several questions (like Sync Google, Outlook Calendar and Contacts) that reference a Google calendar and recommend the use the deprecated Google sync but I am looking to sync to Outlook.com.
Should be pretty easy to do. I use EVO Collaborator for Outlook myself to sync Outlook.com to my Outlook (as well as other services) And I sync contacts,calendar and mails.
You can try it out and see if it works for you :)
A blogpost on syncing Outlook and Outlook.com here : http://outlookandmacosxserver.blogspot.com/2015/06/how-to-sync-windows-live-hotmail.html
The tutorial Sync calendar and contacts using Outlook.com shows step by step how to sync Outlook to Outlook.com. From first glance it will appear that it is pulling information from Outlook.com into Outlook but you will discover that it is indeed "pushing" up to Outlook.com.