The last few winters I've just had one fairly light LS jersey. I hardly ever wore it. Then, last winter, when I was riding almost every day, I _did_ wear it alot, because I couldn't be so selective about weather conditions. (The coldest it gets here is about 25F, but then it often warms up to 45F- so then the LS is too warm!!) I liked it so much, on the days that it was cold enough, that I bought two on clearance this spring, that I haven't gotten to wear yet- another Terry lightweight one, and the Terry Polarfleece soft cuddly one. I am looking forward to cold weather! But if I could only afford one thing, a Bolero or LS jersey, the Bolero is much more versatile, plus you aren't stuck in it if it gets warmer than you thought it would.
I think they are a _lot_ warmer than SS jerseys- because my arms are what gets cold, and they are covered up! Also, I can push the sleeves up if I'm a little too warm.
Another really versatile item is a nice lightweight wind jacket- small enough to go in a pocket when you get warm.
Something I bought but always end up wearing a jacket instead is a wind vest. If you need wind protection- your arms need it too. It just doesn't really add much warmth at all.
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"...I'm like the cycling version of the guy in Flowers for Algernon." Mike Magnuson