I tend to skimp a bit on the upper layer, rather than spending a million bucks on heavy high-tech outer layers. Throw a bit more at layers underneath, as others have said. A thin merino long sleeve shirt goes on first, followed by a Marmot fleece jacket and then a light spray top. A standard Mountain Design (?) pair of waterproof trousers down below over the top of merino long johns. With gloves etc it keeps you warm even when doing the old Shorthanded Sailing Association offshore winter series, which included overnight racing and windy racing in the dead of winter.
I've been lent a really high tech outer layer and it was great, but too heavy and $$$y. The expensive outer layer is also a bit limited in use, whereas the other stuff is useful for skiing or cold days ashore.....which means that here in Canberra we use it a lot!
One trap I once found was having thermals with cotton cuffs. 95% of the thermal
almost dried out quickly - but it sucked the water out of the cotton cuffs and the whole thing stayed damp. Stupid design. Details count, and simplicity is sometimes the best detail.
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