Yesterady, it was a 25 degrees when I left at 6 am. Dark and cold. This morning was 11 degrees colder, it was 14 degrees!!!

However, I was armed with info from yesterday on where the cold can slip in. Yesterday, on the return leg (8 miles) temps down to about 23 and windy, I had to stop to warm my hands midway and feet were getting a tad cold too.

Knowing all that, and that it was 14 degrees out, I put on more gear..Gloves first, I went with my extreme cold motorcycle gloves, with liners..On the long underwear, I went with two layers of US ARMY COLD WEATHER ISSUE BOTTOMS, then a super heavyweight longjohn, and topped that off with UA Coldgear Leggins, and my Pearl Izum shorts..I doubled my socks. Up top, 5 layers and my cool looking wool Army Ike jacket, and a fleece face mask.

Now, it took me almost half hour to put on all the gear, and once I got it on, I rushed outside.. Sheesh, I stuck my fist out at the 14 degrees ! I am smiling big time doing about 20 mph on a flat, with it being pitch dark and cold..My hands were warm, the super cold weather gloves with wool liners did its job. The double socks was right on the money too..To be honest, toward the end, the cold was trying to sneak in. But, all and all, the commute this morning at 14 degrees was an adventure...

At work, it took me about 30 minutes to get that gear off and put on work clothes too...

Insane & Impressive. I'm not sure I'll get out on my bike when it dips below freezing. But then, I'm in the south.

I have rode the motorcycle in as low as 9 degrees..

It was 15 degrees in this pic..

https://www.cehoward.net/snow.jpg

Man, that's a lot of gear!

I ride in a pair of thermal tights(The C9 stuff from target), a pair of regular jeans down below. A light wicking shirt, fleece half-zip and rain jacket above(Pit zips open) Headband for the ears, two pairs of socks and a pair of gloves. That's for down to about 20(My current coldest is 22). By 2 miles in, I have the jacket halfway open and the fleece zipped down as far as it goes.

About the only thing I need to work on are my gloves, mine are fine down to about 35 without wind. If it's colder, or windy and cold, my hands are frozen. I also keep meaning to pick up a pair of clear motocycle glasses(Cheaper than the bike version!) to keep my eyes from watering when I'm not wearing sunglasses.

Edit: I will add that the smartwool socks I got for Christmas are awesome, and the best present I got! I stopped doubling up my socks and they stay toasty down to about 30. We'll see how they do come colder weather.

zrane: try picking up clear safety glasses. at $2-8 bucks a pair... they are cheapper then other options.

I am wondering if the beginners do more trial and error and error more on the "too many layers" side of stuff until they get used to the cold and can have less layers.

Thoughts?

grats!
It looks like you're making use of what you have on hand.

I think you'd find that you can get away with thinner/fewer layers if you have a wind-proof shell top and bottom.
At 10 degrees I usually have mid-weight tights and a pear izumi rain shell on bottom, and two layers (thin "tech" underlayer and mid-weight polar fleece) up top with my showers pass elite rain shell to keep the wind out. For my head I use a thin balaclava with a polar fleece headband, and a windstopper neck gaitor (only below 15 or so). Otherwise, backcountry ski gloves and Keen "Austin" casual shoes with cleats, and hiking socks.

I start out a little chilly, but by the time I'm in an aerobic groove, I'm plenty warm.

Probably. Also, people are more comfortable at different temps. I'm fine in cold temperatures as long as my hands, feet and ears are warm. Doesn't take much to warm up the ears, but hands have been problematic for me. I'll try out the safety glasses, that's a good idea.

I think people are more reluctant to shed layers than they should be. It was 38 this morning. I rode in jeans, t-shirt+fleece with gloves and the ear warmer and it was fine.

I would agree on reluctant. I dont liek to stop and shed layers but I learned a technique from another commuter. He told me if I get too warm, roll up on sleeves a little to expose my wrists. It will cool you down. And it works!

I've found this to be true for me, as well.

As the temps transition from Summer to Fall to Winter, I find that I start out with perhaps one more layer (or simply with a thicker single layer), and will shift to fewer (and thinner) layers as I get more accustomed to the cold.
I also try to remember what I have learned year to year and apply it with each new winter season (what did I find myself wearing when it was 12 degrees last year?).

It is all relative, in my experience of it. The first ride of the season at the freezing mark feels chilly. By the end of winter, temps in the low 30's feel GREAT.