Upper respiratory inflammation usually limits my rides in cold, dry weather. I'll occasionally wear a surgical mask or other face covering to keep my breath warm and moist, but it can hinder hard efforts. At best I can maintain a tempo pace, but usually prefer a lower effort ride if I need a mask to avoid drying out my sinuses and throat. My nasal passages and throat are still a bit scratchy from a Wednesday night ride when the temps dipped into the 30s.
I have cycling apparel for any temperature so it's been fairly easy to stay comfortable. But we don't get many seriously cold days in this part of Texas. Occasionally I've ridden down into the 20s but usually prefer the 40s or above.
The hard part is keeping the feet and hands warm. I've found a combination of socks, shoe covers, and layered gloves to keep the extremities reasonably warm-ish.
I've had exercise induced asthma since childhood, so that's another challenge. It was so bad in autumn/winter 2019 I quit all fast club rides and cut way back on casual group rides. I was a geyser of snot and it was unpleasant even for me. I didn't want to subject other folks to my endless spitting and snot rockets, even hanging off the back.
Fortunately this spring I got some new and effective nasal and bronchial inhaler from my immunologist. Really helps. And my ENT doc suggested cutting back or eliminating the dairy, especially milk and ice cream. Sure nuff, within a week I had much less congestion and post-nasal drip. I didn't realize how much some dairy product were causing my congestion and phlegm. Too bad because I liked chocolate milk, and needed the extra vitamin D and calcium.
I'm still trying to find a non-dairy substitute I like as well. Silk is meh and overpriced. I tried Zone Perfect stuff, a mixture of coconut "milk" with whey protein (which doesn't seem to cause much problem) that's pretty good. Nice texture and flavor.