One of the common dilemmas for a man is how many shoes should be enough for his wardrobe. Anything between 6-8 pairs of shoes should be enough to cover several occasions that may require dressing up.
As a starter, three pairs of Oxford shoes are a must to have. Two Black (a plain toe and cap toe) and a Brown in either quarter brogue or half brogue or a wingtip should be right.
Two pairs of Derby shoes; one black and one brown in any style will do. There is a trend amongst the younger people to experiment with shades of brown like the Tan or Cognac. Then there are the ones who want to stand apart and break away with colors like Burgundy, Grey, Olive, and Blue. These are now becoming more acceptable to be worn around the town, and are more of a casual option.
Two pair of loafers. The first and the most versatile is the Penny Loafer. They are simple and stylish. They can facilitate a casual as well as a semi-formal occasion with equal flair. A pair of Tassel loafers in brown is a great pair to pair up with chinos and jeans. They perk up your style and finesse.
Monkstraps is a category which gaining much popularity. They come in single or double straps. They mimic an Oxford in fit yet ensembles a casual yet ultra chic look. The metrosexual male has a couple of monk strap shoes in his wardrobe for those occasions where he wears them with sports jackets and chinos or khakis.
To lengthen the life of your shoes, I suggest avoiding wearing the same pair of shoes two days in a row. Also, let any pair you have recently worn rest for around 48 hours before wearing them again. It's essential to have shoe trees inserted in your shoes to keep them dry and smelling fresh for your next wear.