Layering is the key.
Layer 0: Body hair and too much chocolate.
Layer 1: Undies and socks (optional).
Layer 2: Jeans, tee shirt and boots/shoes. Shorts may be OK in summer. This is standard summer evening wear for me when in the obs.
Layer 3: Flannelette shirt.
Layer 4: Windstopper jacket and maybe a beanie.
Layer 5: Thermals. The trick is to install these under Layer 2 when conditions are appropriate.
... and Ugg boots.
Layer 6: Throat coat and fingerless woolen gloves.
Layer 7: Freezer jacket.
Layer 8: Freezer boots. Often get to this layer in winter in Oberon.
Layer 9: Freezer Pants and snow gloves. Sometimes get here in winter in Oberon, but not since I've had the obs
.
Layer 10: Heat packs installed inside Layers 7 through 9... never had to resort to this...
Al.