This is a topic near and dear to me, living in SE Wisconsin. As a commuter, taking a shower at work in the morning, with a ~35-40 minute ride, I never worried a lot about it, and tended to overdress. When I did an R12, riding a 200k each month through the winter, I discovered that overdressing is a real problem. Looking at what some of the "influencers" on social media tend to wear, I realized just how overdressed I was. It also helped to read about Velocio climbing the Alps bare chested on sunny days in the winter.
Like others, my clothing choice depends on how long I plan to be out. It also depends on, in addition to temperature, whether there is wind and/or moisture. Though, realistically, if there is cold, wind, and wet, I'm probably not riding outside. I have always been an advocate of wool, but I find that all my wool base layers quickly get wet and stay wet. Even my wool Brynje fishnet shirt seems to really hang on to the moisture. I also have a Brynje synthetic fishnet and will go for that if I'm planning to be out for a while. If it's not too windy, then just a ls wool jersey on that is good to pretty cold temps. If there's some wind, I might add a wind vest. Or, my Supplex jacket over a good base layer. For base layers, I have a few synthetic ones that I've picked up, from Pearl Izumi and I forget what else, that are surprisingly warm. The Pearl Izumi one, in particular, is shockingly warm just by itself, and doesn't seem to hang on to the moisture too much. For my legs, it's similar, though the base is always wool and usually either it's just the wool or some wind-blocking knickers. I have some light XC ski pants that I use on cold, windy rides, that are very nice. For many years my standard outer top was a wool jacket with a wind-blocking front. As noted, that helps keep the back from getting too sweaty, but I find the zipper front to be awkward. A light vest with mesh on the back serves the same purpose for me, and it has the added bonus of being easy to stash in the handlebar bag if I decide I'm getting too warm.
That last point might be the most important. I remember, probably in something Grant wrote, about eskimo who would be constantly removing and then putting back on their seal coats as they worked, managing their body temps and sweat. It is so helpful to be able to remove layers while riding, then have them available to put back on when you stop or slow down or the conditions change. Keep your base layer from getting wet and you're way ahead on staying comfortable.
Also, don't overlook the choice of headwear. Something that feels cozy for 15 minutes in the cold is probably too warm for a longer ride. Likewise, hands and feet. I generally find that my hands and head should feel chilly at the beginning of a ride. Otherwise, as my body temp goes up from the effort, my hat and gloves very quickly get soaked. I only wear a wool beanie below 40, and I use a couple of layers for gloves so I can adjust as needed. Also, below freezing I use a lycra neck gator that I can pull over my chin if needed. For really cold weather, I have a wool balaclava, but haven't needed that the last few winters.
Lastly ... important advice I read somewhere ... 3 layers, base, insulation, outer. Base needs to stay dry, insulation needs to stay functional, and outer is to protect from wind and moisture without keeping moisture inside. I find I don't need all three layers until it is really cold. Cold enough that, now that I'm on the wrong side of 60, I find excuses not to ride. So, it's either base and shell or base and insulation most of the time, with the shell often just being a vest.
Okay, this was way too long - Eric, the outfit you picture would work for me for mid-20's, dry, and not too windy, at a moderate effort. The vest would come off pretty quickly. +1 on Woolie Boolies.
Ted Durant
Milwaukee, WI USA