A couple of notes about brand preferences and what works for me and what doesn't work.
On base layers, these days I buy most of my tops from either Brooks Running or Sporthill. Both of them I can highly recommend and they sell good stuff that is frequently discounted.
https://www.sporthill.com/https://www.brooksrunning.com/Sporthill also sells some actual cycling clothing which is also quite good if you are into actual cycling clothes. Brooks has more Hi-Vis clothing choices which is of course important as well.
For bottoms, I'll usually bring some long underwear bottoms and wear them over the padded bike shorts possibly with a pair of shorts over them. Or I'll bring some tights. Sporthill and a few other brands have some "relaxed fit" tights that are excellent for fast forward sports like cycling or cross-country skiing.
I cross-country ski as well so a lot of clothing that will cross over is welcome. In particular Swix sells nice pants focused for cross-country skiing that also work pretty well on the bike.
On wind shells, I've found that there is a pretty delicate balance between windproofness and breathability. The Patagonia Houdini products hit that balance the best for me, with Montbell's wind shells a close second. Both Montbell and Patagonia make "stretchy" versions that are usually a little better for a cyclist than the non-stretchy versions, which can flap annoyingly on a fast downhill. Wind shells have an enormous warmth-to-weight ratio, usually the highest warmth-to-weight ratio you'll see in any of your clothing. Which makes them pretty valuable. When you dress in layers usually you'll find you do most of the temperature control by taking off or putting on one layer -- for me that layer is a wind shell 99 percent of the time.
Every now and then Patagonia makes a somewhat heavier wind shell with a "fast forward" design where the back and shoulders are made with a less windproof and stretchy fabric. These are great if you can find one. When I say "somewhat heavier" typically they weigh in at about half a pound.
Sporthill makes wind shells but usually they are lined with a wicking base layer. Their shells are inexpensive but somewhat heavier and I find they don't breathe as well as the other options.
Montbell's stuff is great but, being a Japanese company, you should keep in mind that their sizing is also "Japanese" so bulky Americans should choose one size up. Montbell's wind pants are really the best choice if you can get them and want to spend the money. The only thing about Montbell is that their fabrics are a little less breathable than Patagonia's. Usually I solve this by washing the garment three or four times to remove the DWR coating (that you don't need or want).
For less money and more weight Nike and others sell less expensive wind pants on Amazon.
On padded shorts, I usually like to ride with triathlon shorts, which I can find from various no-name companies on Amazon. Triathlon shorts on the average have less padding but have better ventilation and dry out quickly.
Shower's Pass makes nice waterproof gloves that are excellent for those cold and soggy days. Their waterproof socks work but I don't often carry them unless I know the trip is going to be very wet.
Montbell makes a nice oversized bandana. An oversized bandana can be worn on your head under your helmet, can be also used as a hot pad and towel in camp. Which makes it a good multi-use item.
For insulated jackets, there are a lot of good choices out there at varying price points. I prefer synthetics because you are a lot more likely to get the jacket a bit wet than a sleeping bag (where down is usually the best choice). I also prefer pullover-style jackets, my reasoning being that you are likely at some point to wear the jacket to bed and it is easier and more comfortable sleeping without a zipper going all the way down the front.
You should have a fleece or wool hat. Get one big enough that you can pull it down over your forehead and eyes when sleeping.
Raingear is a tough one. Bluntly none of the materials or whiz-bang technologies in use at any price point work particularly well. If you are in a hard continuous rainstorm and working hard you are going to get wet. Having said that there are a number of observations: (1) waterproof/breathable fabrics stop breathing well at higher temperatures, for me usually above about fifty degrees the breathability goes way down; (2) waterproof/breathable fabrics stop breathing when the shell fabric "wets out"; and (3) when water droplets bead on the outside of the jacket, that's great but your jacket won't be able to breathe through those water droplets.
For the money, you can get the best performance from Frogg Toggs. Now Frogg Toggs are ugly, shapeless, and not very durable. But they cost around $30 at Wal-Mart and perform as well (from a waterproofness and breathability standpoint) as garments costing eight times as much. So something to think about.
