Blue:
No way am I getting involved in something like that
Just throwaway the corporate polos, buy some from Valentino, buy coordinated leather accessories, avoid trainers and manmade fabrics and you'll both be fine
PWD:
There's an apparently true story about an English Duke, dishevelled as only a traditional English aristocrat can be without being arrested for vagrancy. His sister called him a disgrace and that he ought to dress in a manner more befitting his position. He replied: "what ever for? Everyone knows me in the village so it does not matter. No one knows me in London, so it does not matter!"
Image? Armando now sports a goatee and a long ponytail (I'm not convinced about either) and sometimes sees important corporate clients in motorcycle leathers. Nowadays he can get away with it. I can shop in via Spiga with a clear concience