ATGATT. Commute year round 14mi each way. Work from home if it is >90F or <30F w/ precipitation.
I wear my ultra business casual clothes (jeans) under my 1-pc Roadcrafter. Keep a pair of street shoes at work but often don't bother removing my boots out of laziness.
In cooler weather I wear a primaloft jacket. Below 50F I use a Gerbings heated jacket and a fleece neck gaiter or balaclava. Keep a fleece jacket at work.
On rainy days, I bring an extra set of gloves so I have a dry pair for the ride home.
On hot days, I'll strip to my undershirt for the ride home and wear a Buff soaked in cold water around my neck.
Laptop/lunch in an Aerostich messenger bag. If I exercise at work, I bring those clothes and running shoes in a tank bag. Leave a camp towel and a bottle of Dr. Bronners at work.
Today, we had a surprise thunderstorm during morning commute. Should have packed an extra pair of underwear. Roadcrafters can leak in the crotch during heavy rain.