What I really like about winter is the heavy knitwear, and using different garments for layers to stay warm during the colder days. A personal favorite is the turtleneck in a soft merino wool or cashmere, combined with a pair of old school flannel trousers and a sport coat with a heavier fabric.
Some days, it is just cold and the rain is falling outside. Having the proper clothing during these days, which includes a serious raincoat and umbrella will make your day a lot better. If you are unsure about which raincoat to get, the trench coat will always be a true wardrobe classic.
I know, I know, beige and white are not the colors that you expected to wear for fall and winter. It will rain and snow and you will get wet and dirty, and you will curse that you wore them. Well, this will eventually happen for all light colored garments and your local dry cleaner will still have an job thanks to you. If you dare to wear them, you will not only look like as a true gentleman, you will also be the best looking lad on the streets.