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

Notify of

Inline Feedbacks
View all comments

Well said Simon, I might have suggrsted the whole cut straight away, but as it’s a first investment, I think that the shoe you pose in the picture is quite a great choice for something that hits all targets.



Hi Simon, great advice. I was wondering, what is your opinion on plain cap toe vs. punched cap toe? I feel that they are both equally versatile, while punched toe adding a bit more visual interest over the cap toe.


The punched cap toe is inherently less formal than a plain cap toe. More broguing (punches) equales less formality.


dont bother with whole cuts as they are expensive, check out the sargeant sale page, they have plain brogues otherwise known as gibson, last time out bout 100 notes, really well made for the office and also casual as the plain brogue is a shoe famous for going with levis and sta prest. brogues are perfectly ok for the office, no one cares



Great advise as always, but given that the Duke of Cambridge wore a black wingtip with his double breast dinner jacket the evening of his wedding, credence has been lent to expanding up on the typical patent options for formal wear. I still support your suggestion that a plain cap toe is the best answer to the question posed by the reader.


Hi Simon,
I agree with your advice.
Now, a general remark: the more I ponder on the range of the current British shoe styles, the closer I come to find them boring! Of course, as many of you out there, I do like and value the craftsmanship behind these products. But once one is unable to afford the big jump into bespoke or MTO shoes, its tediousness becomes obvious. And to be honest, I am really flabbergasted at this fact. And as you all know, this boredom is not skipped over by just introducing bold colours or antiquing old ones. No, it is a matter of style. And strangely enough, in this respect well known old styles seem to have been burried for ever! Even simple variations or sub-styles within, say, the semi-brogue type are less and less easy to find. Two quick examples: the Crockett & Jones’ Malton or the Edward Green’s Asquith: two utter variations of the semi-brogue as can be. And yet, they now seem out of reach to many shoemakers!Isn’t it wierd?
So I wonder whether there isn’t a way to challenge these shoemakers to become bolder again while sticking to the time-honored craftsmanship that justifies our continuous interest in their products?


Dear Simon

On a totally different note, having just returned from a weekend away, the problem of taking and carrying several pairs of shoes, obviously to go with different outfits, led me to think of purchasing a shoe carrier bag. A quick Google search reveals that such an item does exist but oh dear, the quality is so poor and the look so cheap.
Do you know, or can recommend such a shoe travel bag that you have come across?
And finally, how do you take away several pairs of shoes when going away for formal and casual functions spread over several days?
As always – excellent web site and we did miss you when you went on holiday which i hope was pleasurable? Though i am not sure if we can allow you to escape again!
Best wishes


I think the cap-toe falls between two stools – it is not quite formal enough for black tie events, for example, yet it is too conservative to wear casually. It also looks rather boring, in my opinion. Whereas a whole-cut black Oxford is definitely formal enough for black tie, looks more manly than opera pumps, is more versatile than patent Oxfords, and as you point out, it looks sharper than the cap-toe. If you are in a situation formal enough that black Oxfords are de rigeur, isn’t it *better* to be on the sharper, more formal side of things?

So, I would go for whole-cut plain black Oxfords as a first shoe. They will do any formal event, any work event, and cover more bases than the cap-toe.


I finally got round to purchasing my shoes. I took Simon’s advice and bought a plain cap toe from Gaziano & Girling. I’m very pleased with them and they should serve me well for years to come.


Joshua Jacobs

Hello Simon,
I recently visited Mario Bemer in Florence and asked about his rubber-injected soles, and how they are affected by rain. I live in a place where the pavement is often wet, and most of my shoes have a rubber sole affixed to the leather sole (though not extending back to the heel). I asked the very kind sales associate at MB if and how these rubber-injected soles are damaged by moisture, and his response that the shoes are returned for re-soling less often than typical leather-soled shoes. I am wondering if you have tested MBs shoes with these rubber-injections, and if so, what your review is? Thank you.