Whether you wear bike-specific clothing or not is a personal decision and you'll find just as many opinions here as there are users. Read "Just Ride" by Grant Petersen and see if that helps you make up your mind; it did me. While I choose not to ride in bike-specific clothing, I have very specific criteria for what I ride in. Our Conn winters are similar to your Jersey winters.

I ride an upright Dutch-style bike to work. It's an 8-mile commute one-way. I'm not training for anything, so I take my time. I do work up a little bit of sweat on my ride, but I'm not dripping from exertion when I get to work.

I bought a Columbia jacket last year at a popular discount clothing store for about $60. The jacket liner has that silvery "omni-heat" and separates from the shell. Both have pit-zips. I thinks pit-zips are essential for regulating temperature when riding. So, IMO, there's two good points about jackets: 1) separate shell and liner; 2) pit-zips.

Below 25 degrees, I wear water-proof winter boots on the bike and throw my regular shoes in my bag to switch at work. They're not special bike boots, though; I wear them for snow-clearing and general winter use, as well. They're not bike-specific, they're cold-specific.

I use a thermal base layer under my pants on really cold days. Again, nothing special, nothing bike-specific.

My sole concession to bike-specific is gloves. I've tried regular gloves and they all suck when it comes to wind-resistance. In the dead of winter I use Giro 100 Proof gloves AND wind shields on my handlebars.

Others have described their trial-and-error methods. I know I've been down that route, also. I didn't think Carhartt was suitable as it didn't meet any of my requirements for regulating heat mid-ride. Ultimately it comes down to experimentation to find what's best for you and you're riding requirements.