Warm weather: Riding Sport side zip breeches. I have chocolate, smoke blue, and tan. Polo (any brand) or some technical wicking fabric shirt, like the kerrits and riding sport ones, but always with a collar. Ariat paddock boots with riding sport suede 1/2 chaps or my old Ariat Hunter dress boots.
Cold weather: Same breeches, or any polar fleece lined breeches, long sleeve polo or turtleneck with vest, or turtleneck with sweatshirt or fleece pullover. For really cold weather, I love cuddleduds under layers. Middleburg fleece lined tall boots, or Ariat winter paddocs (really old) and 1/2 chaps. Vest or Lands End Sqall, depending on temps. I have an original Mountain Horse coat that is just too dang heavy to ride in, but its great when I have to stand around the barn for other reasons.
SSG gloves, either crochet back for warm weather or the Winter Ranchers for cold temps.
Always, my IRH Air 10 helmet with hairnet. Although hair is not long enough for a ponytail, I hate having it stick out all over the place.