For 90% of men, the colour of shoes is not something they spend much time thinking about. That’s because in most parts of the world there is a dominant colour of dress shoe that is safe, conservative, and generally considered to go with everything. In Anglo-Saxon countries and much of the business world beyond, that colour is black. Men wear black shoes (and more depressingly, black socks) with everything. No one will take offence, no one will consider it a personal statement; no one will notice.
In much of southern Europe, particularly Italy and Spain, that dominant colour is brown. Also in some parts of the US. Some Italians make it a point of pride that they don’t own any black shoes – though when pressed it will often turn out they have one, if only for black tie. And some Italians, it must be admitted, will wear brown every day because they don’t want to think about their shoes, as much as my lazy commuting colleagues in London just wear black.
There is a lot of room for personal expression and experimentation in shoe leather, so it’s a real shame to stick to one colour. But men also easily get it wrong – primarily by wearing tan shoes with dark suits. Light-coloured shoes are wonderful and beautiful. But the occasions when they can be worn formally are rare. This is because of the first guideline to consider (not rule, not convention, but guideline) when picking your shoes in the morning: they should be as dark or darker than the trousers they are worn with.
That’s why it works that some men wear the same colour everyday – they always wear very dark suits, so black or very dark brown will go with them everyday. No risk, no statement.
Let’s explore this guideline a little further. If you’re going to wear brown shoes, keep them very dark (say the colour of plain chocolate) for your first pair. That will go wonderfully with navy, grey and any more casual colour like tan gabardine or green tweed. Try polishing them with black as well, particularly on the toe and heel. They will never look black, no matter how many times you apply that polish – just a deeper brown.
Then, if you want tan shoes (and you should) then make sure to only wear them with mid-grey or even paler cloths. If a suit that light is too much for you, opt for pale grey trousers with a blue blazer or some other odd jacket. For colours between tan and dark chocolate, just bear in mind the colour of the trousers and don’t stray too far from the same shade in your shoes.
(Of course, all this advice only applies to smart or dress wear. Tan is one of the best colours to wear with dark denim, but casual wear is outside the scope of this column.)
As to other colours, red is a great next choice and goes best with navy. The more conservative you are, the darker the red should be. Oxblood being the darkest of these. At its best, oxblood can look darker than black and a lot more interesting. And I personally recommend that the brighter the red of your shoes, the simpler the combination above should be – navy suit, white shirt, navy tie being the obvious one.
Hopefully that arms you to make some stylish choices. Colour combinations in shoes are not difficult. Generally I think navy is best with brown and charcoal best with black, while grey really needs a middle-order brown. But this is more personal choice.