Your post,with its modular theme, reinforced the dual nature of my usual clothing regime for autumn canoeing. To elaborate:
In camp, I replace paddling gloves with light wool. Since I don't pack a pot gripper, the wool provides the dexterity and heat resistance for handling stove and pot. If I'm planning to use much wood/fire, I'll include one, or sometimes a pair of leather gloves.
For traveling footware, I use "Workboots" from NRS. These have an integral neoprene sock and are comfortable until some intangible combination of water and air temperatures dips into the mid-forties. "Sealskinz waterblockers" add warmth when temps or exertion levels fall off. My feet are generally warmer when portaging , so routes dominated by paddling often call for the waterblockers. In camp I'll switch to wool socks and a pair of athletic shoes. I'm careful about keeping these dry.
During my last October canoe trip, I brought five leg garments. In camp I wore a baselayer, covered with a pair of Reeds, and if still cold, which I was during a couple of the mornings and evenings, I layered over with supplex shorts. Traveling, I wore some combination of Epic pants, the supplex shorts, and a homemade pair of 3/4 length silnylon pants. I used the shorts alone on two mid-seventy afternoons, but usually wore them over the Epic pants. For the intermittent rain during two of our travel days, I layered the 3/4s over the Epic. The 3/4s kept my thighs dry while paddling, and the bottom hook and loop gusset adjustment allowed me to hike the 3/4s and other layer, up to mid thigh, tighten and secure for wet landings. This may sound like a hassle, but takes only a few seconds. The fabrics avoid saturation and I have a view of the tops of the waterblockers if I'm wearing them. Ironically, the waterproof socks reduce the depth of water in which I can land or depart a portage. The top of the socks limit water depth to a realistic nine to twelve inches; without them I won't wet my pants until depth reaches mid-thigh. Generally speaking the three traveling garments didn't see any in camp use, and the base/Reed didn't see the route.
With a few regular exceptions, (rain parka) the same was basically true for the five (base, LS supplex, Epic windshirt, synthetic parka, WP parka ,torso garments. The baselayer and parka in camp, the supplex, windshirt, and parka for travel.
Given my interest in a dry baselayer, socks, and insulating parka, I don't know that there is a way around this dualism. (Yea, yea, Hig and Erin.) In fact, we're thinking of adding a power stretch layer to the garment list. I could see PS as a warm substitute (probably too warm) for the supplex layer. But in the case of an surprise immersion, it might give us a few more minutes.