Wow, good question. But a complicated one. There are so many choices. How cold do you intend to ride in? Freezing? Around 20 degrees? Colder? Cycling is hard to dress for because you have wind chill at speed, then can easily overheat when climbing.
The Zephrr JacketLayering is the key. When it聮s in the 30s, I start with a midweight long-sleeve jersey or top, such as 聮s Midweight Long Sleeve Crew ($30). Maybe throw a regular short-sleeve jersey over that for a little extra. Over that I like 聮s Zephrr Jacket ($75). Midweight tights such as the Vello Thermal Tights ($70). And midweight gloves聴I recently referenced the Silkweight Windstopper Gloves ($30) for a guy going to Everest, and they also are what I wear when it is chilly on a bike. Great gloves.
When freezing down to 25, I like a little heavier pair of tights聴聮s Radiator ($60) are a great buy in a very warm tight. For a base layer, I swear by wool聴聮s BodyFit2 60 Crew ($80) is dynamite. Over that, if dry, the Zephrr. For gloves, maybe the Mistral III ($50).
If it聮s really cold, then a wool short-sleeve T under the long-sleeve T like 聮s Merino 2 T-shirt ($65) adds a lot of warmth. A beefier jacket聴the Elite 2.0 ($230), which uses eVent fabric so it聮s great in the wet too. Pants? Pearl Izumi聮s Amfib Tight ($100), which are windproof and lightly insulated. Pearl Izumi for gloves, too, their Barrier Lobster Glove ($70), which are waterproof and insulated.
I聮ve biked in the low 20s with basically Combination Two. You聮ll need to experiment a bit and see what works. Once you聮ve got some trips under your belt, you can start to fine tune your gear in five-degree increments.