Wearing all grey doesn’t have to leave you looking like Regis Philbin mid-90’s. Play with texture. Here a grey and black horizontal striped sweater (Target, Merino wool), white B² button down, grey herringbone sportcoat (Agnès B.), grey Donegal tweed trousers, and a tweed charcoal grey herringbone tie (J. Crew) are casual enough for a cold Friday.
Also of note: the sportcoat is a good example of the French cut, with a very square and boxy silhouette.
Just out of picture: brown shell cordovan wingtips, custom through R. Martegani.