I always wear boots, and prefer lug soles because they are a bit more non slip.
I prefer deerskin gloves in moderate weather because they don't get stiff after being wet. I've had the same pair for more than 12 years ($10 at Lowes). Turn them inside out when new and trim off the excess next to the seams, and they are as comfy as driving gloves.
In cold weather I multi layer with a leather jacket on top. Last year I was too fat for my leather jackets, and I found that a synthetic textile jacket kept me as warm, if not warmer than the leather. I have insulated leather and insulated thinsulate gauntlet gloves. The thinsulate are warmer and lighter.
Cool to moderate cold, I wear chaps and long johns under my jeans. Very cold, I have lined leather over pants that zip from hip to ankle for on/off ease.
I wear a half helmet, and a stocking type cap pulled over my ears works to keep the ears warm. Below 30°, I wear a neoprene face cover that I don't like much. I'm good for about 200 miles in low 20's cold before I'm ready to quit.