Here's my essential list, though depending upon what you do in life yours may be different:
1 -2 Belly bands - I didn't have one with my first pregnancy, but I LIVED in one for most of my first trimester during this pregnancy. You can make this. Stay tuned for information on that one.
2 pairs Jeans - I bought a pair from Gap for pregnancy #1 which sadly didn't fit for pregnancy #2, but a good pair or two of jeans are worth the money if you hang out in jeans all day long like I do.
Comfy underwear - seriously. Your current ones probably won't fit by mid second trimester. I recommend ones that don't have seams down the side. You spend a lot of time sleeping on your side and the seams will dig into you.
Yoga pants - or another pair of comfy pants to wear around the house.
Jacket - if you're going to be pregnant during the winter, acquiring a jacket that fits is a really, really, good idea. I bought one on clearance on a whim during pregnancy #1 and it was the BEST idea. Polar fleece from Old Navy not the warmest jacket, but I live in Texas and pregnancy makes me hot.
Comfy flats - your feet will swell. Some of those sneaker mary janes are great. I taught in a pair for the last trimester. Decently comfy and they stretched as my feet swelled during the day.
I think that's all for my essential list. Granted you need tops, but depending upon what you do for a living you'd need different kinds. I had maybe 5 by the end of pregnancy #1 which I rotated through two skirts for at least a month. I don't think I still have any of those shirts or skirts anymore I was so sick of them by the day I gave birth.
One more thing, you'll be wearing your maternity clothes a bit past d-day so finding some that would double as a nursing top is always a bonus.
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