The life of a shoe mirrors that of a man; there's a pinching arrogance initially, experience then eases it into comfort zones, and finally it lives to tell a story of travel and adventure. If we talk classics, I recommend the Salvatore Ferragamo classic calfskin brogues, the Tod's Gommino loafer, Gucci's glossy leather shoe with a brushed-gold buckle, Paul Smith's striped sneakers and Bottega Veneta's iconic Intrecciato-weavedesign driving shoe.
In terms of styles, brogues (or Oxfords as they are popularly referred to) are the last word in formal shoes, one which no man can go wrong with. Breaking the monotony of neutral shades in a corporate man's wardrobe, loafers bring in just the right amount of colours. For a relaxed evening after a day of running about, one should slip into comfortable lounge-wear. This could include leather slippers and sandals in soothing colours like brown, cream and grey. For days better spent at golf courses, one's collection must boast of a few pairs of spunky leather and fabric sneakers. Finally, one should have at least two good pairs of rugged boots that stick it out on jungle safaris and bike trips into the mountains.
Just as a bespoke suit fits and feels like heaven, a made-to-measure shoe is a yardstick in comfort and class. Shoemakers like Ferragamo and Gucci are adding that bounce in your walk by offering exclusive pieces where the stitching, leather tanning and hues are yours to choose from.
Luxury shoe brands like Paul Smith and Tod's provide shoe-care kits that comprise of beeswax apart from the right buffing and application apparatus. It isn't wise to use one brand's kit on another's shoes. Stick to what comes with the shoe and follow the instructions suggested. A moisture free stowage and a cleaning session after every couple of weeks is recommended for the long life of your shoe.