The best of both worlds? An Alfred Sargent Armfield
Dear Simon,

I have a quick question regarding black shoes that I thought you might be able to help with. I’m thinking of investing in a good pair of versatile black shoes that I can wear for business and also for formal occasions. Is a whole cut the best option? I have a feeling that the ‘cleaner’ the shoe the better when it comes to black, and that wing tips or even simple toe caps may be distracting or not smart enough. Any insights you could share would be greatly appreciated.


Hi Christopher,

First, let’s start with the theory. A pair of shoes, like many things in a man’s wardrobe, is considered smarter the simpler and sleeker it is. So you are right in your instinct that a wing tip or cap toe is less formal than a whole cut. Both have an extra section of leather across the toe and interrupt the otherwise clean upper.

The biggest difference, however, is the amount of broguing involved. By serrating the edges of these layers of leather, punching rows of holes in them, and possibly adding a medallion on the toe, the broguing can turn an otherwise clean and simple cap toe into a complicated design. And brogues are definitely casual – they were invented for bog hopping, after all.

A nice black brogue is still perfectly appropriate for the office. Indeed, a brogued wing-tip is the archetypal English business shoe. But it would not be appropriate for formal occasions, as you hope your next purchase to be (and I applaud you for making the investment, by the way).

However, take away the broguing, and the simple cap toe is a very smart, formal shoe – perhaps, the best of both worlds. Add some black silk laces for those formal occasions (most bespoke shoemakers stock them, as does ASuitable Wardrobe) and it will dress up very nicely.

A whole cut also works, but it can sometimes look a little too sharp, a little too aggressive. It may stand out for more than its quality. I have a whole cut, Decos from Gaziano & Girling, which I wear for formal occasions, but then I also have more black shoes. As a first investment, a cap toe might be the right choice.

I hope that helps