I was sitting outside in a downpour and 50 degree temperatures all day today, while the sailors drifted through slow races in winds of 3 to 5 knots, interspersed with long periods of no wind whatsoever. It's a glamour profession, coaching sailing. Here's what gear I wore, and how it performed.
I wore LL Bean wool & cotton long johns under a pair of fuzzy sweatpants and my Gore-Tex shell pants. Those Gore-Tex shell pants are a few years old now, and are absolutely terrific. The long johns are perhaps 10 years old. Starting to get a little bit saggy, but they work great. My legs were dry and warm all day.
I wore Smartwool socks and my street shoes (similar, but not identical, to these). The Smartwools are great, but I discovered that if I wear my waterproof rubber booties, my feet are dry but cold, and the Smartwools don't help when the circulation starts to slow down in my feet. So today I chose my sheepskin-lined Uggs, even though they're not waterproof. This I came to regret by the end of the day. The waterlogged shoes were probably warmer than any other footwear would have been when this wet, but I need to treat them with waterproofing material, or get a different kind of boot for being in the motorboat on cold, wet days like today. Or maybe Gore-Tex socks. Hmmm.
I wore a wifebeater tank top under a lightweight silk thermal undershirt, under a new insulated fleecey top that I got on sale at the LL Bean outlet store. I was afraid I might be too hot, but nope. On top of that I wore a Patagonia spraytop, designed for kayaking, with a neoprene seal around the neck that leaked steadily. My shoulders and chest were pretty damp after an hour or so out there. I think the layers were the right combination, except for the leaky top.
On my head I wore a windblocking, water resistant fleece hat. It worked great; my head was warm all day. When I came in and pulled it off the hair on my head was dry. I was pretty impressed; I hadn't believed that fleece could really be water resistant.
On my hands I wore fleece gloves. They were sopping wet after the first hour or so, and I would make my hands into fists and squeeze the water out of the gloves as though I were wringing out a wet washcloth. Not sure if there was a net gain from wearing them, but I think so.
When I got in on shore I put on a lightweight synthetic down jacket that I'd considered wearing out on the water (and perhaps will tomorrow). It was just the ticket: light and soft and cozy, and I warmed up quickly once I got it on.
In conclusion: I'm pretty well set for a long, cold day outside in the rain, but could use a better footwear solution and a really good waterproof jacket. Now, in the hotel room, my shoes and tops are draped over the heater. I hope they'll dry by tomorrow.