If you only own one pair of... black dress shoes
Apologies first for the paucity of posts in the last month - work has been rather all-consuming, but also the fact that I leave the house so seldom these days has sort of taken the wind out of my sails for writing about shoes.
This will be the start of an occasional series in which I imagine a world in my aim is not to furiously acquire as many shoes as humanly possible and then leave them to gather dust on a shelf, but rather rationalise and reduce my collection to its core concepts and themes.
The first pair I'll be looking at will be a style that has fallen out of favour in the last few years, and for which Covid may well have been the killing blow - the black dress shoe.
The stock response in this is that you need a pair of calf leather wholecut Oxfords. They can work in the office; polished up they can work with a tuxedo too. These Carmina wholecuts are fine examples, on the pretty sleek looking Rain last.
There is a certain amount of truth here, but keep in mind that the black wholecut is essentially the second most formal shoe (after a patent wholecut) - to my eye, the level of formality can make them hard to fit into any remotely casual outfit. They go poorly with anything that isn't a suit, and since most people have very little need to wear a suit these days, that really hits their versatility.
Keep it smooth
Your inclination might be to mix up the rather rote look of a black dress shoe with a textured or more unusual-looking leather choice. I wrote here about how you might achieve that, and how you can use other materials to soften the formality of black.
You can see the effect of a grain leather here (and obviously a fairly weighty and chunky style) with these John Lobbs:
The effect of colour mixing, with this classic model from Stefano Bemer:
Or the softening effect achieved with a suede, as seen in these Crockett & Jones:
I like all of these shoes and think they all have their uses, but for our "one shoe" - we really need the versatility of a pair that will work for the office, the shops or a funeral. So it will have to be a smooth, black calf leather.
Chuck the brogues
The black wingtip brogue is a shoe that is tricky to place - often too casual for many of the occasions you want a black shoe, but the black leather makes it too fussy for a casual outfit.
The pair below are Cheaney's higher-end Imperial collection. A respectably made shoe certainly, but too difficult to place in an outfit to recommend as your only black pair. On this basis, I think we can say that our "One pair" won't be brogues.
Conversely, if you were to have only one brown dress shoe, I think wingtip brogues would be a solid choice.
A classic captoe?
An undoubtedly solid choice is a simple captoe oxford - I've reviewed the Edward Green Chelsea before, with the black model pictured below.
The Chelsea (while confusingly named for an Oxford shoe) is a fantastic design - very modest in its detailing, with a signature swan neck stitch on the facing. Check my captoe Oxford showdown here for some options from more affordable makers though.
Not my preferred choice in this discussion, but certainly a solid silver medallist.
A wildcard winner - the refined Derby
All of the above, though, was a mere distraction from what I think the real winner is here: a simply styled plain toe derby in a smooth black calf leather.
The pair below are from John Lobb St. James (the venerable bespoke maker rather than the Hermes owned John Lobb). They are the only bespoke pair that I've actually kept after buying on eBay - you can read about the trials and tribulations of buying used bespoke shoes here (mostly trials, to be honest, unless you have time and money to burn).
So why derby shoes? The additional material of the quarters atop the shoe's vamp adds an inherent "chunkiness" to a derby shoe's profile when compared to an Oxford. That doesn't have to make them clunky or heavy looking - the plain toe maintains a sense of aesthetic sleekness,
It's a style that will suit a ...suit, but dress down quite pleasingly with some olive or navy chinos. I'd probably draw the line at jeans, but I struggle to tolerate any dress shoes with jeans.
In the not unlikely event that John Lobb's bespoke prices are just a tad steep for you, many other makers will produce similar designs.