In base layers, jerseys or windbreakers, look for designs with wind-resistant materials on the chest but breathable material in the underarms and along the back, or at least along the sides if the back also has wind resistant material.
Pearl Izumi used to make baselayers with a thicker wind resistant material along the chest. I don't know if they still make those. A few long sleeve jerseys are made similarly, but availability varies from season to season.
Regarding merino wool, while it's good stuff it isn't magical. My 1970s wool shorts and jersey was comfortable pretty much year 'round in Southern California, even in cool rain. But it isn't wind resistant at all. In ye olden days of the pro tour, before gilets and team cars available to hand out and retrieve layers, racers stuffed newspaper under their wool jerseys after cresting the mountains for the fast and chilly blast downhill. Contemporary designs are much better. I don't even wear merino wool anymore. Good synthetic wicking fabrics are as good or better, and much easier to maintain. It washes easily, dries quicker and doesn't need to be stretched to shape and laid flat on a towel to dry for hours.
This $23 Outto cycling jacket turned out to be remarkably good for the money. Wind resistant front and back, breathable mesh fabric along the sides and underarms. I wore it on an early morning group ride that started with temperature in the mid-30s and warmed up to the 50s after a couple of hours. I wore a long sleeve baselayer under it, nothing else. So if it got too warm I was stuck with unzipping but nothing else -- I had no backpack or bag to stuff it in, and it's a little too bulky to roll up and stuff into a jersey pocket. But it was comfortable the entire ride.
When I got home I was surprised to discover the black mesh fabric was soaked (the day was sunny and dry). Even the rear pockets of the same material were soaked, even though they weren't in direct contact with the inner liner. Apparently the fleece lining of the wind resistant material wicked the sweat toward the black mesh breathable fabric. The fleece liner wasn't wet and I never felt wet or clammy the entire ride. Eventually the sweat would have evaporated from the mesh fabric. This jacket should be perfect for our winters with temps in the 20s-50s.
Before this year, on every cool weather ride I toted an ultra-thin Pearl Izumi Select Barrier Jacket, basically a windbreaker. The main advantage is it rolls up small enough to stuff into a jersey pocket, or water bottle cage. The downside is this type of material never really breathes, no matter what the makers claim -- same with my heavy duty Shimano Storm Jacket. It's fancy plastic. It's a good windbreaker, and while the Pearl Izumi jacket soaks through in precipitation heavier than fog, it stays warm because it's windproof. But I get just as wet from sweating inside the jacket. No such problem with the Outto jacket, which also has more and better pockets, including two zipper pockets.