It's real personal. Some people are more sensitive to the cold than others. And it depends on how you acclimate.
Take today for instance. 63°F, winds 10MPH off the lake. I was chilly to start in regular shorts and jersey, but warmed up as I rode. Everyone I saw on bikes was wearing more than I. One girl had on a winter coat with a scarf. A coat and scarf at temperatures some people I know keep their A/C set at.
Anyway, this is the time of year when I start to acclimate. I use the same rule as I do the dead of winter--one that I learned here in this forum: Start the ride feeling a little chilly, maybe even worrying that you're underdressed. If you warm up before a mile, you're wearing too much and will certainly sweat through in no time. If you're not warm yet after two miles, you're wearing too little.
The way that works out is that one morning last week in lower 50s, I wore a baselayer top, armwarmers and a regular jersey, regular shorts and knee warmers below. I did pretty good. In winter, that same combo will get me to the lower 40s or upper 30s. Add tights and a windbreaker and I'm good to the mid-teens.
But, if I don't acclimate and I layer up now--like that chick I saw today--it's hopeless when winter gets here. So I let myself get a little colder than is comfortable now, so that in the dead of winter I don't have to dress like the Michelin man.
In winter, say the 20s to the upper teens, I wear a baselayer, long sleeve jersey, and windbreaker on top, shorts, kneewarmers and tights on the bottom. Double-glove and winter cycling boots. Like this:
I know that doesn't specifically answer your question, but I hope it shows you that only your own experience can answer it. Clothing is the toughest thing to get right in the winter--and probably the most important thing to get right too.
Some people will dress the same way I do and sweat through at the same temperatures. Others will freeze before they're out the door. There's no way someone on the Internet can say how you'll do.
Edit: That's also why there's a bewildering array of cold weather gear out there. Everyone is different.
As for the jackets you asked about, the windbreaker is exactly that. There's no insulation or lining. There is some insulation and a lining in a thermal jacket.