Let's see.
Let's say a woman - Jane - weighs 180 pounds (she's been hitting the ice cream a lot). Her stiletto heels each touch the ground in two places, for a total of four. Let's say the front part is 3 inches by 2 inches, and stiletto is half a square inch (we're estimating here). That's a total of 6.5 square inches a foot, or 13 inches square touching the ground. That's an average of 13.84 pounds per square inch of pressure.
Now for the elephant, Janette. We'll try and cut this as close as possible, and say that she's an Asian elephant, which according to Wiki, weigh between 6,50011,000 pounds. Let's say 6500 pounds is accurate, again, to make this as close as possible (I'm rigging the results as much as I can, because it'd be too easy if we chose a giant bull African elephant
) An Asian elephants foot is
pretty big, and for the sake of argument, let's say it's perfectly circular, and roughly 1 foot across. That gives us a radius of six inches, and an area of 113.09 inches per foot. And an elephant has 4 feet, so that's a total of 452.38 inches. That comes out to 14.36 pounds per square inch.
Which is actually pretty close. But again, we kind of rigged the results - we chose a light elephant, and a heavy woman. If the woman weighed 120 pounds, the average would be something like 9.23 lbs/foot. And if the elephant was a bit bigger (even for an Asian elephant, still) at around 10000 lbs, the average would be something like 22.10 pounds per inch, over twice as much. (Although I suppose we could compensate by saying the bigger elephant has a bigger foot...giving him an extra inch around the foot, that'd still be 18.84 pounds per square inch)
In short: it's plausible, but you kind of have to cheat a little with the numbers to make it work. (Or feed all the elephant's food to the woman, to decrease his weight and increase hers
)
Hopefully I didn't just make a fool out of myself by messing up basic algebra....
) 
