I think at 30 I'm still in just long sleeves and gloves I'd overheat in a vest. I have the same Brooks vest you do for cooler temps (teens) and a mountain hardwear ghost vest (maybe?) for wind. I'm a big wool fan, personally. Coldest run I did last year was in my ibex dress and thermal tights!

A trick for bottoms, though -I'll often later a summer running skort over running tights if it's really cold because the extra layers keep the skin on your butt from getting too cold.

(just saw your brooks is the jacket. I have some sort of brooks vest that I think is similar. When I find it I'll figure out what it is)