The once popular sporting and hunting boots in 1850s have now become appropriate to wear in town. They are easily identified by their open-styled lacing, allowing these shoes for a wider fit.

Contrary to popular belief, derby shoes are not constructed only for formal occassions. The semi casual construction of these shoes also allows one to wear them casually when strolling around town in style.

A little fun fact; brogues were initially designed in scotland with real holes to drain out water. Nowadays those perforations on the shoes' upper gives them a distinctive character that other smart shoes lack.

Perfect for contemporary gentlemen anywhere, brogue shoes are all about versatility. By being less formal than the previous Derby shoes, they are perfect for work - for example in a laid-back offices.

Wear them with your favorite three-piece suit, or go for casual yet refined look with a white button-up shirt and rolled-up dark denim jeans, brogue shoes can never be wrong.

As classic as it gets. Penny loafers sports a leather strap across the top of the shoe, with a slot just wide enough to hold a small coin. A theory states that the slots were used by American students to hold coins for making phone call. Either that is true or not, penny loafers is the ideal choice for going smart casual.

These legend pair of shoes are by far the best choice if you are going for a casual party. Yes you can still wear your suit, even put that vest on before, but make sure for the bottom half you wear a nice slim-fitted pair of chinos or corduroys. Sock or no sock is absolutely your choice, but as the writer I personally recommend no sock.