Rab Strata with Polartec Alpha - Pretty much the ideal cool to cold weather climbing jacket. Doesn't get stuffy when you're working hard, but warm enough for belaying. Hood fits over a slim profile helmet. Great for biking when it's cold too. Not as ideal if you just want to wear it for idling.
Asolo Reston WP boots - They're so comfortable and lightweight. I originally bought these for winter day hikes when my serious double boots are overkill and I find myself wearing them every day. Could be a bit more breathable, but for day use it's not a big deal.
Petzl Tikka RXP - This is the new, smaller headlamp with Petzl's Reactive Lighting tech. I love it. It's a bit heavier than the popular headlamps these days but if you have a lot of hiking to do in the dark this one is the bee's knees. It automatically adjusts its output between two different LEDs so that it can light up the trail at your feet and the trail off in the distance easily. This is one headlamp you don't have to fiddle with. You can lock it into various outputs if you have tricky lighting conditions but it's rarely needed.
Zpacks Multipack - The perfect complement to nearly any pack. It can be a pack lid, huge hip pocket, summit pack, or man-purse.
R1 Hoody - Still my favorite fleece thing. The hood and the wrist gaiters make it more appealing to wear in cold weather than any other fleece I own. The Power Dry gridded fleece keeps me comfortable in changing conditions even when I'm working hard.
Fleece, fleece, fleece - With a few thrift/consignment shop finds, fleece has again risen to the top of my favorite clothes. They breathe better, dry faster, and wear harder than synthetic fill, the only problem being bulk. Even then, fleece vests don't take that much space and do wonders for cold weather comfort. Must be paired with some sort of wind-resistance though.
Uniqlo UL Down Parka - At $69 this jacket is simply outstanding. The low price point of this and other Uniqlo stuff (fleece, fleece-lined pants) has enabled me to expose more people to cold weather hiking and backpacking.