^^^^
I also own several pair of Frye boots. Again, they can be extremely comfy. I gave D a pair as a gift as a '‘going to college’ gift. She went to a rural type campus…much walking. She has worn them for 6 years, they are on the 3 pair of soles…and still going strong.
You are probably right about certain areas of CA. But Silicon Valley is the antithesis of status clothing. Hey…10 grey T-shirts and a few pairs of Levi’s …and your set with your work wardrobe. Add a sweater and your good for an evening out.
Don’t forget your Reef flip flops.