Eric,
You may have the same problem as I do. I would describe my symptoms identically and have done numerous posts at two periods over the last couple of years to diagnose it.
Do you have packaway top (removeable frame) or permanently mounted top (scissors or Michelotti depending on year) that folds into the boot? I happen to have the packaway top frame and from what I can tell have a soft top that was not the right one for the car. I bought it through a repair shop and Moss Distributor that is now out of business and they ordered and installed it for me 4 years ago. Told me that it would stretch out. It doesn't so they were b.s.ing me to keep from having to buy new top or do work over. Over time, tops get tighter not looser, though as Kim says, some good hot sunshine will loosen them a little.
Whichever top you have, it is likely the wrong top for the particular frame and car year you have. People change the top frame set-ups a lot and my guess is the wrong frame can get on different cars if you aren't careful. There are the pack-away frames, like mine, the early scissors type permanent frame and the later Michelotti permanent frame. The pack-away frame is slightly taller than the others and I think they got the wrong top for me. If you have a pack-away you may have the same problem. If not, it still sounds like either the wrong top for your car or one that does not fit due to poor manufacturing. The top should come down and fit closely to the top of the windows in that rececssed area so the top flap covers the top edge of the window. With pack-away frame you may be able to grind down the ends of the frame to lower the frame but since you can't adjust the header fit at the same time since it is glued on I am leery of doing that as it may end up fitting too loose. At least now, it is tight enough and doesn't flap in the wind.
I bought a new one through Chris Roop who gives 20% discount. There may also be a top sale still on at Moss which may save you a couple more percent on top of that if you get it through Chris who is really good guy and very knowledgeable. When it comes I am fitting it myself very carefully and checking fit before installing.
If you do end up getting new one, consider the one with the zip down rear window as it's very nice on direct sun, too hot days to have top up but rear window down and lots of air moving.
I have lived with mine as is for 4 years as I try to put the top up only when I have to anyway and it doesn't rain much in the arid mountain west...as I am in Denver. When I have been in a gully washer I just stuff golf towels in the cracks. So...depending on how frequently it rains and your intended use pattern you may be able to do without changing it if you need to.