Hey @jokenjin - welcome! I know where you're coming from as I live in Naperville.
I do a lot of walking around my neighborhood during the week although, to sounds cooler, I call it "urban hiking" LOL. For the short (3-4 mile) walks around the neighborhood, I have a pair of base layer running tights and fleece lined trekking pants. Actually, I wear that for longer hikes on the weekends (10-15 miles), too.
I find that as long as my torso, hands, and feet are warm, I am good to go. My typical layering for the upper body is my sun hoodie as a base (I like that the hood can keep wind off the back of my neck while being thin enough to fit under my beanie), maybe an additional performance tee over top of that, my fleece, followed by my puffy. That provides more than enough warmth and, more importantly, wind protection.
I just bought a new pair of REI glove liners to add additional warmth and wicking capability to my winter gloves. Since I use trekking poles 99% of the time on the weekend hikes, I need something to keep the tips of my fingers warm since they're not moving around that much while gripping the pole.
Finally for my feet, I just picked up a pair of insulated Merrel boots and wear them with a pair of sock liners and Merino wool socks.
That has kept me really comfortable so far this year and we're not likely to see daytime temps in the low teens this year (according to NOAA), so that should be adequate for the whole season.
I think the last piece of important gear is a good daypack. The key to remaining comfortable in our area is being able to layer and, as you get warmer through the day, having a place to store any layers that you shed.
Lots of fun trails in the area - enjoy the winter!
“Between every two pine trees there is a door leading to a new way of life.” (John Muir)
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