My toes never get warmer on a ride. From the time I start a ride to the time I finish, my toes are in a steady temperature decline.

My "trick" is to simply start warmer. I put my winter cycling boots (Shimano MW80s) on the radiator at night, so they're toasty warm when I put them on in the morning. Compared to putting them on cold after they've been sitting in an unheated garage all night, it makes a huge difference. When I put on cold boots, my toes will last about 30 minutes before they start to hurt. When I start with warm boots, it's more like 90 minutes. My commute is 90 minutes, so that's just about perfect.