Clothing is a tough one.
Active
1. cotton is death cloth in cooler weather
2. base layer ... think synthetic underwear
3. mid layer ... light fleece (thicker in winter)
4. outer ... wind layer (wind proofed shell)

Passive
1. fewer layers
2. thicker
3. low activity ... walking a dog for example

Check out Costco .... they have excellent merino wool underwear on sale .... it's very soft.