I've got at least 5 sets of gloves to wear in differing temperatures and other weather conditions. I prefer not to ride in the rain, but some of my warmer gloves are reasonably water resistant if I get caught in a shower. In the cooler seasons, I often carry an extra set of gloves while commuting because the weather is often very different during my morning and afternoon commutes. It is not unusual to have 30-degree swings in temperature between my morning and afternoon rides.

I generally wear Pearl Izumi Cyclone gloves in temperatures ranging from the 40s to low 60s. They are also reasonably water resistant. For colder temperatures in 20s and 30s, I wear Pearl Izumi Softshell gloves. In the teens and low 20s, I wear PI AmFibs. The AmFibs are the closest to being waterproof, but my hands sweat a lot in them if the temps get above freezing.