Some email providers won't let you send messages larger than a certain size. Adding pictures and large attachments to your message can prevent you from sending that message (and any messages sent after the large message). To check if you have an email that has a large attachment, do the following:
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Go to your Outbox, and then open the stuck email messages. Start with the oldest message first.
Note: When you're online and email works normally, you won't see the Outbox. The Outbox appears at the top of the sidebar only when messages are waiting to be sent.
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If the message has an attachment, check the attachment size. If it's larger than 5MB, delete the attachment and either attach a smaller file or a link to the attachment.
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Once you delete the attachment, test Outlook. If you continue to have problems, repeat the process until you've checked all messages in your Outbox.
More information on attaching files in Outlook email messages...
