This was me last summer! I was using a shield too and every time I went out I had to think about what I was going to wear and be able to feed in public comfortably. The shield makes it harder.
I found big loose flowy tops were best. I'd put the shield on first. Then get baby into place. I'd lift my top and then use it to cover the side of my belly that would show... Or grab a muslin to wrap around my belly or side for extra coverage. I also wore a singlet underneath a lot, but sometimes it was just too hot!
A friend had a few kaftan type tops that she used and would be able to feed thru the armhole - pulling it to one side (does that make sense)
Good luck. The shield definitely makes it a bit more tricky. I'd fed my other babies without a shield and it certainly wasn't as difficult.
Peachymama have tank tops that are like a bandeau, then have a layer over your b00bs, so you can make the gap for feeding as big or little as you want - they sound similar to the Kmart split style feeding tops (I have not been able to find them at my local!). They also do dresses in the same style and a t-shirt with a layer you lift, then an inner layer you pull to the side - I find the hole for feeding quite big plus they are loose & flowy so you could get the nipple shield in place first , then put baby on. It's about $30 for a top so not too bad price wise.
I had a range of things I used. The kmart tops are good. Sometimes I used a breastfeeding bra and just a singlet that I'd pull down slightly. Kmart and target also have those singlets with the built in bras (they are in the underwear section). I have huge boobs so I wore them mainly around the house.
My friend was a really shy feeder and she had this apron style thing that went around her neck but had wire in it so it was not resting on her chest, allowing the baby to breathe. It gave her total privacy.
Like this one
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