I hate that I have to ask this as I feel it should be obvious, however I grew up in the lower mainland and it does not get very cold here.
Now that my son and I are venturing out in the fall to areas between Merritt, Princeton, Vernon, etc. the weather is not what we're used to and it will only get colder. So far I've been doing ok dressing in layers with Cabela's Rain Suede jacket and pants as an outer with Salomon Quest 4D hiking boots that I use in the summer with warm socks. My son tends to get cold easily which really ruins the hunt for him and makes me feel like a terrible father.
The boots need to be upgraded for sure, feet are starting to get cold. I've been looking at the Irish Setter Elk Tracker boots, Schnee Granite Boots (only 200g insulation), and some lower priced Cabelas brand boots or those in the same ball park.
For myself I don't mind spending the money on a good pair but for my son I try to keep the price lower as he grows out so fast. Usually a pair a season, I scored a good pair of Salomon last year for him at Value Village for $20 bucks.
We have no idea what insulation weight to get for boots. We both wear merino wool long johns, then a pair of hiking pants. We have synthetic or merino wool undershirts, a fleece long sleeve top for over that, then an outer layer, sometimes we'll wear a light down jacket over the fleece and under the outer layer.
We do have gloves, mitts, head gear, etc. We have hand warmers with us when required.
We don't want to be too cold or hot, yet we want to stay warm... I feel like Goldilocks.
Where do we start?