Glad to hear you’re sucking it up and going for a ride when it’s cold. Of course this all depends where you live; if you’re talking about cold feet and live in Phoenix, AZ then you’re a wuss. If you’re talking about cold feet in Anchorage, AK then you’re drinking my sake, Kimosabe!

Resolving cold feet will involve an investment, but frigid tootsies are a fast road to a miserable ride so I think you’ll find the purchase to be worth it.

First, you need to find as thick, wool (or similar synthetic) socks that you can fit into your cycling shoes without having your feet go numb due to the fact that there is now so little room in your shoes. One pair of socks is totally affordable, but shopping around for a dozen pairs to find the right ones will set you back into the triple digits. So shop wisely, feel how thick they are (as in, don’t buy 1/2 inch thick snowboard socks), and hopefully try some one before you buy.

Depending on where you live, investing in some mountain bike shoes is likely a great idea. They are usually slightly larger to allow those warmer socks plus you gain the benefit of traction and studs if you’re a winter, snowy-conditions rider. As a fringe benefit mountain bike cleats engage with the pedals easier if you’re fighting through snow, sleet, ice, and slush. But 9.9 out of 10 times you can work your road cleats/pedals with mountain bike shoes as well.

The thickest, ugliest, biggest pair of neoprene booties are your best friend. They’re a brash effrontery to style, but looking good on a bike when it’s 17F takes less precedence than not loosing your digits to frostbite. Usually in the sub-$100 range, again they’re worth it.

Waterproof shoe covers are a moot point when it’s actually raining. Sure it’s a good way to keep your white shoes white(r), but with water coming down from above and up from below (the road and your tires), your feet are going to get WET. Again, this means big, thick, ugly neoprene booties.

If it’s dry and it’s absolutely frigid, I often slap one of those chemical toe warmer/hand warmer packs on top of your shoes and under the neoprene shoe cover too.

Lastly, as for mere “tricks” like you ask, try to cover up any secret holes in the bottom of your shoes. Often there are more cleat screw holes in the soles of your shoes than are necessary to accommodate all the cleats out there. So either plug them somehow or make sure you have a durable, non-breathable insole to prevent cold wind from venting in and freezing your feet.

Good luck!