Rule #1 with spray skirts is always make sure the grab loop is out.
I make it a habit to always physically grab the loop and hold it in my hand before my boat ever touches the water (usually sliding in from the bank).
I've never liked the idea of a loose skirt -- use the other methods or punch out with your knees against the skirt and certainly practice beforehand.
Hardshell Kayak Sail Rigs
Recreational Kayak Paddle
Paddler's Truck Rack
Canoe Pack Liner
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