The layer principle only works on the basis you actually take them off as well as put them on. Often when cycling we are loath to stop to do that, and even more loath to take off things off when adding a different layer. Adding a windproof / shell warms you up and that might mean removing an insulation layer, before you put them on. But we don’t do this, so overheat, sweat, then chill despite more layers. More flexible layers for wider ranges of conditions often works better in this way as well.
This is for sure a struggle for me. If only I had the bike handling of Sagan and could basically do an entire outfit change while descending at 70kmh.
One thing that did help was leaving the winter jacket for all but the coldest or longest rides. It's mostly because I don't have anywhere to put it unless I'm running a tail fin bag and then I never take it off even when I should. Unless temps will not go over 10, I leave it.
Arm and leg warmers with a wind proof gilet and armless wool base layer just in case have gotten me through a lot and the added benefit that they are easy to get on and off (and in and out of a pocket) so I actually do it. Gilet can be swapped for the Shakedry as needed and they pack down enough to carry both.
Shoe covers though, I can't get it right. The neoprene ones make my feet sweat so bad and the thin waterproof ones breathe well for me, but are so hard to get on and off I usually don't until it's too late and my feet are already wet.
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