One can never go wrong with a combination of classics.
Even though those pictures were shot quite a while ago, I still feel like this is a look I’d pretty much wear again today. Maybe only accentuated by a hat, not a bun, and the shirt tucked into the trousers instad of leaving it as it is.
IRO Paris pants (similar 1, 2),
Ralph Lauren shirt (similar 1, 2, 3 + also nice: 4),
Armani Bag (alternatives 1, 2),
Ray Ban Wayfarer Sunglasses,
Cartier Diamond Bracelet, Cartier Trinity Ring,
Prada brogues (similar 1, 2)