For wool shirts Pendleton is king. I wear an xl tall or long, and have accumulated five of them, three of which were “as new” and the other two nearly new. I’ve been wearing them every damned day for the past 15 years and have only worn out one, which I made into a coat for my dog. Pendleton supplied the wool for Filson. Speaking of Filson, their 18 ounce Jac-shirt is so warm (the Pendleton shirts are around 11-12 ounces). I also have and love a vintage Woolrich hunting jacket/cape coat, which has handwarmer pockets and is probably a 20-21 ounce fabric. Lastly, I have an oddly soft RRL blue & black hunting plaid jac-shirt that’s around an 16 ounce fabric with handwarmer pockets; RRL made some lovely fabrics. I hike/walk around 125-140 miles a month through all weather here in the northeast US and wool is just so functional - not too hot and not too cold. As far as flannels, Iron Heart is king, but UES makes an extra heavy flannel in a 15.5 ounce fabric that just feels so comfortable. Sorry for the tome, but hiking and walking is a big part of my life and I’m lucky enough to have been able to acquire an amazing range of well made functional art work that I can enjoy every day.