I don't think extra skin should impact a caliper reading much, if at all. The calipers measure the millimeters in a pinch of skin to see how much fat you have between the layers of skin. So even if there's excess skin, the calipers will still only measure what's in between your skin layers, not how much total skin you have. If that makes sense?
Before I had my excess skin removed (and there was a lot of it!), I was calipered at 12.5% at my lowest. I'm assuming that all my extra skin didn't affect the reading since I doubt I was any lower than that in reality.
As we get older (I'm 54), our bodies store fat in odd areas. We lose it on our necks and hands (which is why they get so vein-y) and store it around our middles -- the menopot.
Was your caliper test a nine-site? That would give you a more accurate result than a three or four site test that might only be measuring your problem areas.
Regardless, all body fat tests except DEXA scans and dunk tanks are just estimates. And 27% is a perfectly healthy body fat percentage.