I've been experimenting a bit and rounding out my cold weather gear, but here's what I've been using for certain temperature ranges in Illinois this year:
40°**-50*°*F:** Shimano Evolve Wind jacket with a 32° base layer from Costco some reflective leggings I got at Old Navy a few years back (been trying to find them again, but no luck!) with ridign shorts underneath, fingerless riding gloves with a pair of stretchy running gloves over them if it's a little colder
30°**-40*°*F:** Gore C5 Windstopper Jacket with a 32° base layer and sometimes another merino base layer on top. Same leggings and riding shorts, Castelli Estremo gloves, wrap around ear warmers
<20°-30°F: Gore C5 Windstopper with the Shimano Evolve underneath and one or two base layers (sometimes I take the Evolve off if it starts to warm up). Electric heated gloves from Amazon. My fingers get way too cold and uncomfortable without an additional heating source, so these have made cold riding MUCH more bearable (https://www.amazon.com/gp/product/B08HYM99W5/). Heated socks from that same Amazon company with additional toe warmer packets. I haven't upgraded to riding shoes yet, so I haven't bought any shoe covers yet. Polartec Balaclava from Costco.
So far the jackets have been the most expensive part, but the Gore C5 is incredible with just a base layer or two. The biggest challenge for me was numb fingers and toes, so the electric heated gloves and socks have been a game changer for colder mornings. I usually ride for about 2-3 hours and swap layers into my bag as needed.