If ever there was a rule that any stylish and trendy male knows by heart, it is the age-old rule in menswear that reads thus:

Thou shalt match the leather colour of your shoes to the leather colour of your belt.

Some of us follow this rule religiously, while others couldn’t be bothered. But if you want to come across as a stylish, dapper gentleman, you may want to ask certain questions like: Must the colours match all the time? Since fashion rules are not written in stone, are there stylish ways to work around it?

Let me let be your fashion and style guide as we unravel this mystery.

1. The more dressy the outfit and the occasion, the more the necessity that shoes and belt should match.

If you are are wearing a suit, your belt and shoes should match in colour AND leather finish AND texture.
This means you should match black patent leather shoes with black patent leather belt; tan coloured leather belt with tan coloured leather shoes.

Also, dress shoes – derbies, oxfords, brogues – require a dress belt (the buckle should be shinier, and less thick).

2. If you must mix colours, do it with caution.

This is the new rule, and it offers more flexibility than the old one. You may ask, can a light brown belt be matched with dark brown shoes? Fashion stylists maintain that this is just fine.

Playing with different shades of your leather colour — a dark chestnut watch strap, a sandy brown belt, and rich amber lace-ups in patina — all of which are different shades of brown, is a good way to add a slight amount of visual contrast to your outfit, so long as the shades aren’t too far apart.

3. Ultimately, it comes down to the shoes that you are wearing rather than the outfit.

If you are wearing dress shoes, the belt should match. If the shoes are casual, the belt that you choose should coordinate rather than match.

With coordination, take in account the outfit.  Allow yourself experiment with casual shoes – espadrilles, plimsolls, sneakers, boots -, because there are no rigid standards  The only rule is not to wear a dress belt with casual shoes.

If you are wearing casual shoes, the sky is the limit. It just has to coordinate with the outfit.

4. Lastly, as a general rule – at least for the present moment – mixing brown and black is still off-limits.

If it’s incredibly subtle — like if you are wearing black leather shoes and your belt is so dark a shade of brown that, at first glance, it seems to match — then you get a pass, but it is not something you should aim for.  Because black is to brown as water is to oil when it comes to matching shoes and belt in menswear.