Rolling is always more challenging with winter gear due to buoyancy issues. Even my O'Neill neoprene hood significantly makes it harder to get enough momentum to get upside down. I find that it is much easier, however, to come back up with a brace on the same side on which I go over. In that case buoyancy can work to my advantage.
Make sure your ears are protected. Cold water on the eardrum causes dizziness and can even cause ear damage if experienced too often. It is good to practice rolling in cold water, however.
Classic Freestanding Rack
Recreational Kayak Paddle
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