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Good post Billy, I am getting the Sun mountain H20 bag which is waterproof and cuts out the need for an umbrella, and as mentioned I will be also trying the thermal leggings under waterproof trousers this winter. I currently use a helly hanson base layer under my polos and the coolness it gives is great.
I use my old Nike wet weather rugby kit. All of it is well vented as it is designed to be run around in yet it is tough as anything as it has to put up with the rigours of rugby training.