Join Date: Nov 2007
Location: Upstate NY
Bikes: 2013 Trek Domane 5.2; 1986 Cannondale R800
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Don't know much about your build, but since you're posting here I'll assume you already carry a built-in layer of insulation (if you know what I mean...). I draw on years of racing and training and commuting in the Northeast in all weather conditions and I'll comment on your list based on that.
That said, I think at temps over 40 you won't need more than one long sleeve base under a wind jacket. I'd make sure the jacket can be easily opened, with one hand for ventilation. Your inner climate will change a lot as you ascend, or descend hills. You want to be able to quickly and easily open and close the collar and otherwise allow air to pass thru. I got the Gore WindStopper jacket (non-lined) from LL Bean which is otherwise a great jacket. But it's a pain to zip and unzip. Major points off for that.
For us fuller figured gals, bibs are a must. Even tho I have a respectable butt, I'm still yanking up non-bib shorts and tights while I ride. Way too much distraction. Also, I recently picked up a pair of the Assos RX-LL which are great, but not wind-proof. Wish they were even at 40-50 degrees. But I got them at a great price and didn't have many choices at the time.
Skull cap? Don't know how much fur covers your dome, I have a healthy layer there and don't need the cap till it approaches low thirties. Should be noted tho that most heat loss is via the head. You can use that knowledge to your advantage.
Extremities (feet/hands) are, for me, a very personal issue. Years (many years) spent in the Northeast, playing outside as a kid (and grownup) with less than perfect footwear have left my feet very slow to warm up and hard to keep warm. For some reason my hands are comfortable down to 40 or so with regular fingerless riding gloves. But keeping my feet comfortable has been a serious challenge. Two things are most important: circulation and an external heat source. Seems once my feet get cold, they stay that way so I've recently started using those chemical foot warmers under my Assos overshoes. I also fabricated an inner sole made of 1/4" foam rubber that I slide between the shoe and overshoe. I'm not impressed by the Assos boots. Then it's a matter of minimizing constriction. Instead of adding thicker socks (altho EMS has a great thin woolie I really like) inside the shoe, I have a pair of pretty thick woolies I pull over my road shoe, before the Assos boot (which I'm not impressed with, did I mention that?).
For gloves I'm using the Pearl Izumi's. I had great success with their GoreTex winter gloves of the past, but these leave a bit to be desired. Mostly because my hands tend to get too warm, sweat and then the glove becomes almost impossible to get back on once removed. Any moisture on your hands, or in the insulation makes them very hard to slide into. I'd also like more padding in the palms. Or any, there doesn't seem to be any.