Sending, receiving, and organizing email in Outlook.com
Hello
Since this also happens in Outlook.com on the web, it is unlikely to be a local Outlook problem. If messages appear in Sent Items but are never delivered, this may be an account-level or server-side mail-flow issue.
First, check that your Microsoft mailbox/cloud storage is not full:
https://support.microsoft.com/en-us/outlook/can-t-send-or-receive-email-in-outlook-com
Then try sending a simple email with no attachment to yourself and to another provider such as Gmail.