You can always try it and see, but before 144s came out, most dudes who skated more transition had 149s on 8.25s and they worked a treat.
I have one setup right now in that size DLX deck 8.25 x 32 with 14.38 wb and I don't think I would want to go any wider on the trucks, but my usual ride is 8.38 on 149s with two or three washers on the inside of each, so it brings the wheels out more.
In setting up a board, you can leave out washers to not have the trucks seem so wide or if your wheels are skinny, you can get away with a lot narrower deck as the wheels don't sit past the deck line the way wider wheels would.