I know this is a few months later, but maybe I can help. I fought with this for a while. It depends on the mailer you're using, and your code a bit so it would be best to post it here.
Overall though, outlook and hotmail have extremely high spam filters, so there's a list of things you need to consider.
First - I've heard third party mailers will get blacklisted or blocked pretty quickly (check their reviews), so check that the IP address hasn't been blacklisted. You can contact outlook to do this (good luck), or send yourself an e-mail, find your ip in the header of your e-mail, and check a blacklist checker online somewhere.
Second - As part of USA's CAN-SPAM Act of 2003, you need to provide some sort of unsubscribe link as well to be in the good books.
Third - If you are using phpMailer or something along those lines, you'll need to remove anything that looks like this:
$mail->AddReplyTo("youremail@domain.com");
$mail->From = "youremail@ domain.com";
Because that will get it marked as spam.
Fourth - If you end up trying to send your e-mails through your gmail instead, allow access to third party apps, then go here (https://accounts.google.com/b/0/DisplayUnlockCaptcha), it will show up in your hotmail just fine.
Be warned that if you test your hotmail too often with the same message, it'll get blocked again.
Hopefully this helps!