Same issue for me. It never gets below freezing here, but the winter rains and wind are very damp and chilly. So waterproof clothes (combination of storm parkas and storm overalls, ponchos (not good in the wind) and waterproof shoes); warmer clothes, thermal undies, and knit caps; gloves.

Since nights are cold here in the summers, we don't add much in the shelter department - we keep a small tent and a tube tent available for having to camp out, and our sleeping bags stay the same - 3 season - plus space blankets.