Another idea:

Try using the hard backed breast shells with the "sore nipple" rings on the
back instead of the rings usually used for inverted nipples.  Sometimes this
shapes the areola into enough of a conical shape so the baby can latch on.
 After all, this is breastfeeding, not nipple feeding.  I've seen this work
with moms who had truly microscopic nipples.

I have not had the same luck with the soft shell type, although these look
much better under clothes.  With the hard-backed breast shells, you
definitely get the Madonna look.  You know, sort of like the Lady Viking
Opera Singer.  Very distinctive.

Elizabeth