When Helen Hunt enters Jack Nicholson's building after walking in the rain, you can see she is wearing a bra under her shirt, as you can see the straps and the bra closure when she goes through the door. When she gets off the elevator and walks to his door, she is not wearing a bra under the wet T-shirt.
I think she used some kind of brassiere to hold her breasts up during that scene, because clearly, the front of her breasts are exposed but you can see the faint outlines of straps on her shoulders. Maybe she didn't want them to sag down or something.
When the three are driving in the car to meet the ones parents, the top is down. But then they pull over so Helen Hunt and Jack Nicholson can listen to Greg Kinnear;s story the top is up.
That's the whole point. She is soaking wet, and when that happens you can see right though the shirt, even if you have a bra on. That's why she tried to cover them up. There is NO WAY Helen would go bra-less for a scene.
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