I ride up to 15 km. in very cold winter temp. But more typically, it's 8 km. In -10 to -25 degrees C.
I've never worn toe warmers. Nor neoprene booties. But I do wear thickish socks in mountain bike shoes. Other people wear boots and slug along slowly.
Winter riding means you tend to cycle slower because of the cold, ice, snow..
I wear the same winter jacket that I wear for walking or light/not too cold snowshoeing. It is not a cycling jacket at all when it gets very cold. The jacket has pit arm zippers. I prefer in very cold winter temp....this is enough to give you frostbite in the face, to have a jacket that covers part of my bum. Not as short as my cycling jackets.
I have to wear lobster claw winter cycling mitts when it gets very cold.
Wind most definitely affects your body temp. I wear a very light headband over my ears under my helmet. I have a 2nd helmet that has less vents. I've never had the need for a skullcap under helmet.
I've never invested in leg warmers...but if it works, great. I wear light (summer weight) rain pants on top of leggings for double layering + some snow repellency. It works and I don't overheat.
Keep it simple, cheap but in layers. And try to avoid wearing 100% cotton against your body. Something with polyester or polyester-blend, if it isn't wool for breathability /wicking. You don't need to invest in ton of expensive clothing. After all, winter is messy, slushy, etc.



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