Are you hunting at a lodge? If so, you shouldn't need the full blown chaps, unless you prefer them. A simple brush pant or technical pant will suffice; hell I wear solid color Sikta Grinder and Dakota pants for all my upland hunting. Chaps are nice though if you're punching thickets, the grass is really wet, or there are a lot of thistles where you're hunting. For your upper body, a moisture wicking short or long sleeve shirt, with maybe a lightweight upland style shooting shirt and a comfortable fleece/softshell/hoodie will have you covered for most october hunts. If you're doing the typical SD lodge/outfitter style pheasant hunt, In October you're likely walking mostly sorghum/milo strips, CRP grass, and shelter belts. Doubt you'll be punching thick cattails and willows. You'll want a game vest that allows for easy access to shells for reloading. If your walking with guides, the guide dogs will mostly retrieve birds to the guides so they carry quite a few of the birds, but have a vest capable of bird carry. For footwear, a comfortable pair of lightweight waterproof upland or hiking/hunting boots and a set of muck style boots in case it gets really wet & sloppy. I wear Keens unless it's really wet or we start punching cattails. Honestly, at a lot of managed pheasant hunting operations in SD, you can kill birds with comfortable footwear, jeans, and a t- shirt or hoodie and barely break a sweat if you're in shape.