I like reading Velouria's posts on The Lovely Bicycle. She is touching various subjects and her writing is often more technical than you can find on many other, female-authored, bike blogs. However, frequently I get a feeling that she may be complicating things for not much reason.
Just yesterday, she published a post on winter clothing. This is a very comprehensive list of garments she recommends based on her own experience (and clearly she has plenty of it). The list is directed towards those readers of The Lovely Bicycle who seek advice on how to dress up properly for winter conditions. Once I read that list, I started wondering if people who up to this point were considering riding their bikes in winter, but were not yet completely convinced they were ready for it ("It's cold out there!"), are going to be put off by the amount of garments they have to arm themselves with.
(Velouria divided her list into two categories: clothing for transportation cycling and one for a sporty, recreational cycling. I realize that riding for sport requires a more sophisticated gear and instead, I am going to focus on transportation cycling here. I assume that a seasonal cyclist will start his/her year-round cycling this way.)
First, I seriously wonder if you really need all those wool layers. Well, maybe, yes, if you bike more than 40 miles non-stop and air temperature is around -20C (i.e. in negative Fahrenheits). But if it is a mild winter day (meaning -4C or about 25F) and your ride is of a moderate length (10-15mi), I really question that you would have to buy wool underwear because your usual cotton one is not regulating your body temperature well enough. On the other hand, I obviously don't wear bras so I can't comment on this topic.
Also, Velouria recommends skirts since she can easily add some more layers under them if needed. Unfortunately, this is not an option for guys (unless you are Scottish). But I rode my bike at temperatures lower than 10F and I didn't feel that I needed anything else than my usual "winter" pants - thicker corduroy trousers. Oh, and they are made out of cotton. No wool necessary. They are warm enough all the way down to about 5F. That is - on a ~10 mile long bike ride, of course. Again, if you have to ride for something like 40 miles non-stop, you may need something different.
Jackets. It must be really cold (i.e. below 10F) outside to make me put on anything thicker than my usual windbreaker shell. Is an old GoLite jacket (or a waterproof shell) that I bought 10 years ago. It is still in a pretty good condition and travels with me nearly everywhere. It is not warm (has zero insulation) but blocks all the windchill completely to the point that once I rode my bike in winter wearing only this jacket and... a single long-sleeve, cotton shirt (It wasn't freezing that time, of course. Maybe around 25F). In general, I quickly figured out that I am well dressed for a winter ride if I feel cold once I leave my house. After a couple of miles I feel warm already and while a wool baselayer may help, I don't necessarily need it.
The only true "special" clothing that has to be considered in winter is for your feet, hands, and ears. Normally (down to ~15F), I wear my regular leather shoes, just like the rest of the year. But once the temperatures go down or the dry winter (no snow or old frozen snow, clear streets) turns into a wet winter (precipitation, mud, fresh snow) I put my Bogs on. They are perfectly waterproof and keep my feet warm.
Hands need some special attention as well. I found out that what works best are... cheap skiing gloves. Those bulky, thick, bit oversized ones that leave plenty of air pockets around your fingers. They are warmer than special, tightly fitted bike gloves. I tested skiing gloves at temperatures below 10F and they worked well on a short distance ride. I didn't even need a liner inside.
Ears can get frozen quickly. I just wear a head band once I feel that it is too cold to leave the house without it. In general, I avoid hats as my head overheats too quickly, but if it gets really cold (~5F and below) I wear a thin hat (I guess it is made out of wool) under my helmet. That's right - a helmet is my regular winter "hat". Also, on those colder winter days I add a second protection layer for my ears - Rox Dog Earz. They work surprisingly well in insulating my ears from the freezing wind chill.
Rox Dog Earz - extra insulation for your ears in winter.
This all means that on my way to work in winter I do have to take some special care of my feet, hands and ears, but except that, I don't see much need for any other special clothing. The main rule about transportation cycling is to "dress up for the destination, not the ride". In winter we have to add one more rule - "dress up for the end of the ride, not the beginning". Remembering that, I can avoid overheating and still stay warm most of my ride.
So in general, before you spend $200 on that winter Rapha jersey, just open your closet. The perfect winter clothing is probably already there.