Remember that babies breastfeed, they don’t nipplefeed! As long as baby can take a good portion of the breast into his mouth (baby's mouth and gums should bypass the nipple entirely and latch on to the areola), most types of flat or inverted nipples will not cause problems with breastfeeding. Some types of nipples are more difficult for baby to latch on to at first, but in most cases, careful attention to latch and positioning, along with a little patience, will ensure that baby and mother get off to a good start with breastfeeding.

An alert newborn who latches on and sucks well is the best remedy for flat or inverted nipples. It's easiest for baby to learn to latch on in the first day or two after birth, before your milk comes in. Engorgement tends to make flat nipples flatter, which makes learning to latch-on more difficult. Get into bed with your baby quick so you both get lots of practice!

How can I tell if my nipples are flat or inverted?

Instead, you can determine whether or not your nipples are flat or inverted by doing a "pinch" test. Gently compress your areola (the dark area around the nipple) about an inch behind your nipple. If the nipple does not become erect, then it is considered to be flat. If the nipple retracts, or becomes concave, it is considered to be inverted. Inverted or flat nipples will not become erect when stimulated or exposed to cold.
If the nipple becomes erect during the "pinch" test, it is not truly inverted and does not need any special treatment.

Different Types of Inverted and Flat Nipples

• Dimpled: Only part of the nipple protrudes. The nipple can be pulled out but does not stay that way.
• Unilateral: Only one breast has an inverted or flat nipple
• Inverted: There are different possible degrees of nipple inversion.
  
  Grade 1:The inverted nipple is easily pulled out, maintains its projection fairly well without traction. Gentle finger pressure around the areola or gently pinching the skin causes the nipple to pop back out.
  
  Grade II:The inverted nipple can be pulled out, but not as easily as in Grade I. After releasing traction, the nipple tends to fall back and invert again.
  
  Grade III: The nipple is severely retracted and inverted. It is difficult to physically force this nipple out and hold it there.

What can I do?

If you have inverted or flat nipples and are having problems, you can try the following:
(treatment during pregnancy is debatable)

Get breastfeeding off to a good start

• Get help with positioning and latch-on
  Getting skilled help is critical for a mother with inverted or flat nipples. It is important for the baby to learn how to open his mouth wide and bypass the nipple, allowing his gums to close further back on the breast. Experimenting with different positions is a good way to find what is most comfortable for the mother and helps baby latch most effectively. Some mothers find that the football (clutch) hold or cross-cradle hold gives them the most control, which also makes it easier for baby to latch on well.
• Breastfeed early and often
  Plan to breastfeed as soon after birth as possible, and at least every 2-3 hours thereafter. This will help you avoid engorgement, and will allow baby to practice at breastfeeding before the milk becomes more plentiful or "comes in". Lots of practice at breastfeeding while mother's breasts are still soft often helps baby to continue to nurse well, even as the breasts become more firm (which can make a flat nipple more difficult to grasp).

Get a good latch!

When latching your baby on, hold him in close against your body, with his ear, shoulder, and hip in a straight line. Align baby's nose with your nipple. Pull back on your breast tissue to make it easier for him to latch on. Tickle baby's lips with nipple and wait for baby to open wide (like a yawn). Then latch him on, assuring that baby has bypassed the nipple and is far back on the areola. The resulting latch should be off-center -- deeper on the bottom (more breast taken in on the chin side than the nose side). Baby's nose should be touching (but not buried in) the breast, and his lips should be flared out. Make sure the latch is correct see “how to do it” section.(link)

Don’t allow your babe to become upset.

Baby should not associate breastfeeding with unpleasantness. If your baby becomes upset, immediately take a break and calm him. Offer a finger for him to suck on, walk, swaddle, rock, or sing to him. Wait until he is calm before trying again.

Nipple stimulation before feedings.

If the nipple can be grasped, roll the nipple between the thumb and index finger for a minute or two. Afterwards, quickly touch it with a moist, cold cloth or with ice that has been wrapped in a cloth. This method can help the nipple become erect. Avoid prolonged use of ice, as numbing the nipple and areola could inhibit the let-down reflex.

Pull back on the breast tissue during latch-on.

As your hand supports the breast for latch-on with thumb on top and four fingers underneath and behind the areola, pull slightly back on the breast tissue toward the chest wall to help the nipple protrude

Hoffman Technique.

This procedure may help loosen the adhesions at the base of the nipple, and can be used during pregnancy as well as after the birth. Place a thumb on each side of the base of the nipple -- directly at the base of the nipple, not at the edge of the areola. Push in firmly against your breast tissue while at the same time pulling your thumbs away from each other. This will stretch out the nipple and loosen the tightness at the base of the nipple, which will make it move up and outward. Repeat this exercise twice a day, working up to five times a day, moving the thumbs around the base of the nipple.

Nipple Sandwich.

"Make" a nipple. Use the "breast-sandwich" technique to get more breast tissue into baby's mouth. Hold your breast well back on the areola, with your fingers underneath and thumb on top. Press in with thumb and fingers while at the same time pushing back toward your chest wall. This elongates and narrows the areola, which enables baby to latch on more easily. Remember that babies breastfeed, they don’t nipple feed!

Breast Pump.

Use a breast pump to draw out your nipples before feedings. Use the one in the hospital while/ if you’re in a hospital. You can alternatively make your own with a 10 cc disposable syringe.  Remove the plunger, and with a sharp knife cut off a half inch from the nozzle end. Insert the plunger into the cut end of the syringe. Place the uncut open end of the syringe over your nipple so it rests up against your areola. Gently pull on the plunger to draw out your nipple just before putting baby to the breast. See Section on pumping - link
Insert diagram of making own “extractor”

Breast Shells.

Worn inside your bra, breast shells may help draw out flat or inverted nipples. Breast shells are in two pieces and are made out of plastic. The inner piece has a hole that fits over the nipple. The pressure on the tissue around the nipple causes the nipple itself to protrude through the hole. Breast shells may be worn during pregnancy to take advantage of the natural increase of the elasticity of a woman's skin by applying gentle but steady pressure to stretch the underlying adhesions (connective tissue) and draw out the nipple. After birth, they can be worn for about a half an hour before feedings to draw out the nipple. They should not be worn at night, and the milk collected while wearing them should not be saved.
They have two parts: a back with a hole through which the nipple can protrude and a rounded dome that fits inside your bra. Pressure on the shell from your bra against the areola gradually stretches out adhesions and allows the nipple to protrude.

Nipple shield.

If baby continues to have difficulty latching on, try a nipple shield. These are also used for sore nipples. The baby sucks the shield rather than the breast.
A nipple shield is a thin, flexible silicone nipple that is worn over the mother's own nipple. It has holes in the tip to allow milk to flow to the baby. If other strategies are not working, a nipple shield could help baby latch on and nurse well by providing the stimulation to the roof of the baby's mouth that signals his suck reflex. Nipple shields should only be used with the guidance of a lactation professional as they can lead to problems if not used properly.

Nipple Soreness

If nipple soreness occurs it may be due to:

• Discomfort as adhesions stretch (that’s a good thing!)
  Some mothers experience nipple soreness for about the first two weeks of nursing as their flat or inverted nipple(s) are gradually drawn out by baby's suckling. See section on sore nipples and get help if this persists.
• Moisture becoming trapped as nipple inverts after feeding.
  If the nipple retracts after feedings, that skin may remain moist, leading to chapping of the skin. After feeding, pat your nipples dry and apply 100% lanolin preparation for nursing mothers).

When nipple soreness is prolonged

Rarely, a mother may experience persistent sore nipples for a longer period of time because instead of stretching, the adhesions remain tight. This can create a stress point which may lead to cracks or blisters.

When a mother has deeply-embedded nipple, rather than compressing the mother's milk sinuses (milk storage area) under her areola, the baby compresses the buried nipple instead. Because baby is unable to get the nipple correctly positioned in his mouth, he will not receive much milk for his efforts, and nursing will be painful for the mother. In this case an automatic double electric breast pump can help because, rather than compressing the mother's areola, it uses uniform suction from the center of the nipple to draw the nipple out. Over time, this usually works to break the adhesions that are holding the nipple in.

If one breast is easier for baby to grasp and he nurses well from that breast, the mother can continue to feed on that side. The mother can pump the breast with the deeply inverted nipple until the adhesions loosen and the nipple is drawn out. The baby will get all the milk he needs from one breast as long as he is allowed unlimited and unrestricted time at the breast.

If both nipples are deeply inverted, the mother can pump both breasts simultaneously for 15-20 minutes every 2 hours. The mother can feed her baby with an alternative feeding device until her baby is able to latch on effectively and comfortably.

How long a mother will need to pump in order to draw out her nipples depends upon the strength of the adhesions and the degree of inversion. For some mothers, one pumping is enough to completely draw out the nipple. If the nipple continues to deeply invert, the mother may need to continue pumping. When the nipple stays out after pumping, the mother can resume breastfeeding immediately.

Once the mother's nipple can be drawn into the baby's mouth correctly and the baby can breastfeed effectively, the mother should be able to discontinue pumping and breastfeed without discomfort.

Can this story be linked?...

Breastfeeding with less than pointy nipples – by Halfpintpixie!

It can take a bit longer to get it sorted, but breastfeeding with flat nipples is possible and (after a while) even enjoyable & relaxing!

In the hospital where babypixie was born, several “helpful” midwives took it in turn to tell me my nipples were very flat and then to shove, yes shove, said flatties into her little mouth, all the while pushing her head into my breast. And this from a “pro-breast-feeding” hospital! Needless to say, within a few hours, they were bleeding and I was in bits, my nightgown rubbing off them was toe-curling torture!

Luckily, I am stupidly stubborn and persevered. Anyone who so much as glanced in my direction was invited over to check our latch. Everything I read said that the only reason for bleeding nipples was poor latch but ours was fine. Many experts believe it’s to do with adhesions within the nipple needing to stretch and break, that is certainly what it felt like!

It took the best part of 10 weeks to get to the stage where nursing didn’t hurt, and now at 9 months we have no plans to stop anytime soon. We’ve gone from me making a “nipple sandwich” so she had something to latch on to, to her crawling over while I’m asleep, pulling my top down and popping herself on! If someone had told me that on week 2 i would have thought they were mad, and probably given them a good punch.

Do I have any advice for anyone in the same situation? I had read up about flat nipples and breastfeeding while pregnant but never really believed they would cause me hassle.

There are techniques you can do, some your partner can help with  but in my experience a hungry baby, properly latched will sort them out once and for all!

Medical Literature and further info:

Morphologic Study of Nipple-Areola Complex in 600 Breasts.
Aesthetic Plast Surg. 2008 Jul 15. [Epub ahead of print]

Inverted nipples: correction using a simple disposable syringe.
East Afr Med J. 2008 Jan;85(1):51-2. No abstract available.

Nipple aspirator: a self-designed instrument for inverted nipple.
Plast Reconstr Surg. 2008 Mar;121(3):141e-143e. No abstract available.

Medela article on inverted nipples

Breastfeeding basics article on inverted nipples