What does it mean when your boobs and nipples are really itchy everyday?

Candidiasis: You need to see a doctor and get examined to better get a sense of what's going on here. Itchiness is a common symptom for people who have clothing/detergent allergies. Alternatively you could have a fungal/yeast infection call candidiasis, which can be treated with over the counter anti-fungals, but see your MD first.

Itchy boobs: Possible allergies or fungal infection. Consult your doctor.