Posting on behalf of DH because we are both stumped by this. What shoes should/ do men wear with 'smart casual' wear? As in chinos/ cords and a shirt. Sometimes with a jumper over the top. This seems to be the scene in his new office, whereas previously he has always been in uniform, joggers and hoody type plain clothes or occasionally a suit.
He has always tended to be a one pair of shoes at a time guy - he owns a pair of black smart shoes for weddings, funerals and occasional suit-wear, a pair of hiking boots and a pair of flip flops. Otherwise he just has a pair of trainers (usually of a fairly ugly rugged walking style) that he wears for everything else (including outings where he's otherwise dressed semi-smartly 🙄) until they die and he buys another pair. He did branch out and bought a pair of boots not dissimilar to the ones in the picture a few winters ago (and which have lived in the cupboard since) that he has been wearing since he started this job, but he feels they're not right with what he's wearing and also apparently make his feet sweat and his toes numb (which I suspect is because they were very cheap 😂). He bought a pair of brown... things... last week (can only describe them as ancient-grandad type orthotic slip-ons) as an alternative but I have vetoed them.
He is very time-poor at the moment so I have suggested just ordering loads of stuff online and then returning what doesn't work/ isn't comfy, but neither of us is sure what we're aiming for. Needs to be something relatively hard-wearing and comfortable for a lot of walking about in as well as smartish.
Also stumped on colour as his chinos are all darkish blue so black shoes and most brown shoes seem to look odd with them.
Any advice/ pointers/ links from more stylish people than us would be gratefully received!