In short yes of course your shoes and belt should match! Soooooo many men get this simple concept so wrong. My theory is that if you are buying a new pair of shoes you should look at it as a bundle, new shoes, new belt that matches.
I have lots of my clients ask me this question if the belt is brown and the shoes are tan can't I just use that brown belt? No! Tan is tan and requires a tan belt to match the shoes, brown is brown and goes with your brown shoes.
If you are unsure of the shades of brown, there is a simple and very effective way to check if your belt matches the colour of your shoes... hold the belt next to the shoes and see if it is a good match! See so simple, if it is not a match you need to go find a belt that will match your shoes.
Now if you are one of those fancy pants that loves to experiment and go for a deep forest green or navy dress shoe, this can sometimes be trickier to find the matching belt. When this happens I suggest you go online or head down to the trusty Queen Victoria Markets (if you are in Melbourne, if not most cities will have a similar market). You can have a custom belt made up for generally around $30 in a leather that will match your shoe colour and your waist size! Brilliant!!
Now when it comes to casual shoes, try and pair it with a casual belt. Hence don't go wear your black business leather belt with your white Converse trainers... My suggestion is if you have to use a leather belt at least make sure it is textured or suede.
When it comes to boat shoes or loafers these you can generally get away with a more casual belt, but if you can match the colour and the texture this is always going to take you to the next level in your style!