Don't rest until you find a pair of NOS or barely worn old school Florsheim Imperials. The latter in particular can be found for a reasonable price. (Or start with a cheap, knackered pair just to find out what size works for you.) I think black may be easier to find and/or less sought after than brown. Once the soles and heels are gone you might want to change the heels for a combination of leather and rubber but stick with leather soles.

My personal experience is that old school Florsheim are an absolute treat for the feet and look better than anything out there new today. However if you really want to look after your feet and your shoes then you need 2 pairs minimum so you can rest each pair for a day between wears. And maybe a 3rd pair for when one is at the cobblers.

if in London the Loakes are cheapests from Discount Shoes near Victoria.

Not seen in flesh but Berwick do one now https://www.afinepairofshoes.co.uk/collections/brogues-price-desc/products/berwick-1707-long-wing-brogue-black

For me they're work shoes. Utilitarian but not really my cup of tea aesthetics wise. The only black shoes I like are more elegant and to be worn with a suit. Unfortunately I don't own any like that but I would like some.

Got any pics of people doing that look Sid ?

Wearing black longwings with highwater jeans in the UK will inevitably elicit the question "do you like ska mate?" from strangers.  As it happens, I do.

Florsheim Imperials for me as well. I scored a vintage pair nearly new a few years back off ebay for 25 bucks + post. Polish up to a great shine. Can't say I've lived in them due to the seasons here. I can only wear them really in spring and autumn but they do get worn quite a bit then. Need rehealing now but otherwiselike Yuca says seem bullet proof and keep their shape on top really well if you tree em.

The fit is beyond doubt the best of any of my shoes though thats just lucky for me I guess.