TL;DR: If you want to sort your messages by date sent, then pressing Option reveals this option in the sorting dropdown.
My corporate mails started their life on our mail server, visited the ZOHO system, to finally arrive on Google Apps. During one of the migrations the date received field was overwritten by the actual date on every message. This rendered my mailbox useless, but luckily the date sent field was intact so if I sorted with that, the chaos was over.
Last year when the MBP became my main workstation, I finally settled with Apple Mail once again. I found the way to display date sent, in the top right corner of the messages (View > Message Attributes > Date Sent). Still I failed to sort them by it. This led to the some strange situations like this:
I don’t have to say that I didn’t like this a bit. Things like this could come up by various reasons. For example the Google Groups spam filter catches a false positive and the admin approves the message only a few days after. Messages like this could have several days difference in date sent and date received.
Today I found the solution in a superuser question, and finally I could solve my – as it looks – typical Mac problem.
On the above pictures you can see that the messages are sorted by date received. If you click there you get a little menu to choose the sorting option, but there is no date sent option, until you press the Option () button!