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The flower buds of Nipplewort were thought to resemble nipples.  It was therefore expected that its use would help to heal sore nipples.  This theory was known as 'The Doctrine of Signatures'. Briefly, 'The Doctrine of Signatures' came into medicine in the sixteenth century and held that God marked everything he created with some form of sign which would help to direct healers towards finding their cures for ailments.  So, when one looked at this plant, one saw nipples and applied the doctrine.  Many plants which have 'wort' as part of their name would have acquired the name as a result of this doctrine, plants such as Liverwort, Bladderwort, Lungwort would fall into this category. The word 'wort' comes from the Old English 'wyrt' for root or herb. 

Wildflowers of Ireland

Image: Antique Print-LAPSANA COMMUNIS-COMMON NIPPLEWORT-220-Flora Batava-Sepp-1800