There are A LOT of learning curves with breastfeeding and what you should wear really doesn't need to be an added stress.
While I know a lot of mama's are comfortable with breastfeeding in public, I am not. Mostly because I cannot handle the side eye from strangers when I have attempted to do it. The first few times I tried I was less than graceful trying to wrangle my boob out in time before a milk leak stain appeared with my baby screaming at the top of his lungs. By then all eyes were on me and I felt exposed in various ways. Hopefully I will be more comfortable with my breastfeeding skills and be able to gracefully nurse in public instead of in my car (where people still stare at me through my windows -_____- )
I love off the shoulder tops in general but they are extra perfect for breastfeeding. I opted for this white one in case of a milk leak stain it wouldn't be as noticeable. I actual found I would pull the bottom of the fabric up and tuck it into the top of the shirt since it has the elastic top that goes around the bust line/shoulders. It stayed in place nicely during nursing. I wore my favorite strapless nursing bra underneath which is both comfy and super affordable. Shop this whole look below, including my favorite postpartum underwear!
I love a good jumpsuit (if you don't you need to fall in love with one). This color is so fabulous for transitioning into fall and I love the elastic top and waist. This means it will adapt to my body comfortably as it seems to be changing daily in size. The elastic waist isn't overly tight so it doesn't cause any discomfort on my postpartum belly (I am wearing my waist trainer underneath). The tube top type cut allows easy breast access and so far the most graceful way I can nurse. The fabric is breathable for all those fun hormonal heat sweats and I love the loose wide leg. Plus the slider snake print sandals I have linked are seriously the easiest slide ons and most comfortable. No toe rubbing blisters some open toe sliders can cause and you can easily slide your feet in them without any hands (hello multitasking while breastfeeding).
The best part about a black maxi dress is it's easy to layer with multiple pieces....oh and you can't see milk leak stains! Seriously, just when I think I am out of the danger zone for a leakage BAM! I love this black maxi because it's a closet staple but also so friendly for breastfeeding. The straps are thin, stretchy and adjustable so I just drop the strap down my shoulder and the top part follows. I then will drape my new favorite $14 cardigan (pictured) over my baby while I nurse (the fabric is super breathable) or my other new favorite semi sheer velvet burnout kimono (linked in the shop post below). The maxi is a very soft cotton and has some support built in the in the bust so if you're feeling brave you could go bra free! If you also haven't noticed I have been wearing my Portland Leather bag non stop since it goes with everything and is large enough for me to carry my newborn essentials in. I find a large bag that goes with 90% of your outfits is also key to making breastfeeding comfortable. Who wants to worry about carrying two bags while out and about and then having to switch out all your goods to a different bag every day?