Last winter was my first cycling winter. I shocked my Dh by actually getting out there and riding in the cold! Of course, I'm not in a super cold weather state, either. I'm in Southern California, but it can still get chilly in the winter. (Dh chooses to go running when it's cold out to reduce the wind chill factor. Since I abhor running, I don't have that option!)

Lately I've done a couple of cool morning rides where I took my light jacket, which can easily be rolled up and stuffed in my jersey if I get warm. If it's colder than "just a jacket", I add the arm warmers. I usually prefer the jacket first if it's one or the other, I guess because it's easiest to put on and take off, plus it keeps my core a little warmer, not just my arms. But there is the option of the vest as well. If it's even colder than "light jacket and arm warmer" weather, then I add a long sleeve wicking shirt, probably without the arm warmers. I don't have a thicker jacket for cycling, but at 30 degrees, you might want one.

As for legs, I have both leg warmers and exercise pants that I wear over my cycling shorts. If I'm not sure it's cold enough to keep my legs covered for a whole ride, I'll do the leg warmers. If I know there's no chance of it getting warm enough to take them off, I prefer to where pants over my shorts (except now I'm thinking I might should invest in a pair of actual cycling pants!). I just hate the look of my fat bulging where the leg warmer elastic tightens around my thigh under the cycling shorts!

One of the biggest issues for me on the colder days are my ears hurting. I wear what I call a "thief mask". Dh and I wear them snowboarding. It covers my ears and, if I want, my neck and mouth depending on which kind you buy and how you choose to wear it. And then I, of course, where my helmet over it.

I have to say, I was really surprised at how not so miserable a bike ride in the cold can be when you are properly attired! You just have to figure out what works for you.