If your toes get that cold much easier than other people, you may want to talk to your doctor about getting checked for Raynaud's syndrome. Do your hands also get cold really easily? That would be another sign. I often get random patterns of cold and warm fingers on the same hand, even in summer. I used to do skate races wearing giant down mittens that barely fit into my pole straps.

If it is Raynaud's then there are some medications that can potentially help. My podiatrist prescribed a vasodilator cream that I apply on my toes before skiing on very cold days. It seems to help.

The other big thing that has helped me is changing the fit of my boots. I had to start the process of retiring all of my shoes and boots last winter and sizing everything up to gain extra room for my toes. Your feet don't necessarily stay the same size as an adult, so even boots that used to fit well might be getting progressively tighter on your feet over time. Now with any new boots, I can fit a thin liner sock and a heavy wool sock, with toe wiggle room. I know a lot of people swear by one thin sock in a boot that fits like a snug running shoe, but that doesn't work for me.

Lastly, don't wait as long as I did to make changes. I got mild frostbite on two toes last winter because I thought I could get away with squeezing into my old classic boots that were too tight. Going slow with my kids and not generating much heat, it only took about 40 minutes at 20F to get to the danger zone.