I'm only a veteran of one Winter season, but rode almost daily for up to 25 miles last year. It was cold, but entirely manageable, here where it snows to excess along the Lake.
Synthetic base layers are the only way to go, IMHO. Polypro, and more modern blends in tight fitting base layers wick any moisture away from your skin. Cottons and silk just hold the moisture making one cold in short order. On top of the long underwear, I'll put a snug nylon pair of jogging type pants and a pair of Cycle-Cuffs to avoid anything hung up in the drive line. On top, a fleece jacket over the base layer and a nylon windbreaker (again snug). Gore-Tex is substituted for the windbreaker when it's sleeting/freezing rain. Cycling shoes with heavy synthetic fleece socks, or if it's REALLY tough, my hiking boots with the same socks. A pair of extra large ski gloves pulled over my fingerless cycling gloves. Wear the fingerless gloves underneath...you'll be happy to have them when you pull off the ski gloves to make an adjustment or change a flat. Natch', a helmet with either a liner and/or ear covering headband top off this little runway inspired ensemble
I know you don't want to scare the kids, but garments flapping in the wind don't work in the least for me.
Oh, one more Fredly type item to consider: I found a pair of goggles necessary when the wind was whipping across the Lake and making my eyes water to the point of not being able to see!