I realize this may seem a bit silly for the “Equipment Discussions” forum, but I found out recently it makes a difference.
I play in a league one evening a week, and for the past six weeks straight it’s been overcast w/ intermittent light rain (Seattle Sunshine). I have a Sun Mountain Speed Cart, which comes with a screw-in umbrella holder. I was using your basic, generic golf umbrella, which worked well enough, until we had a little wind. The loose fit of the handle in the holder, combined with the non-vented umbrella, meant that it didn’t take much wind to lift it right out of the holder.
I then bought a Sun Mountain umbrella, and it’s working much better. The handle is a snug fit in the holder, and the umbrella is vented which should reduce the aerodynamic lift. It’s heavier and larger in diameter than my old one. $30 well-spent.