Shoes, as well as being the things that keep dirt and water off your socks, are an important part of dressing right. Footwear can be the absolute highlight of an outfit, and in turn can be the most likely to throw an entire look off. Picking out the right shoes, and stopping them from going prematurely shabby, is a consummate art.
The first step is to consider what goes with what, and make sure you have the right gear in your arsenal. The brown Brogue is a classic that can work with almost any suit, particularly those that are in a lighter shade. Or you can upscale to the Brogue boot, which goes well with jeans, shooting tweeds and other outdoorsy clothing. Another all round, multi-purpose winner is the black Oxford, which The Mitchelli writes is "the most versatile shoe a man can own".
On the more casual or smart casual side, blue suede gives a good mix of comfiness and sharpness, and having it on Chukka boots gives you the extra sole if a bit of long distance stomping might be a part of your day. Chukkas were originally used as boots for British infantry in the desert, so you can generally count on them to last a good long time. Loafers are good for the very casual end of things, and are a good complement to shorts and short sleeved shirt combinations, with their ability to go without socks. Of course you might want to also invest in a good pair of trainers, for when you're getting active.
A pair each of Brogues, Chukkas, Loafers, Oxfords and trainers should mean that you are never left wanting in the shoe department for any occasion. Make sure that your shoes match the colour of your belt, and complement the colour schemes for the rest of your wardrobe. Once bought, you can keep your shoes lasting longer and looking better by getting shoe trees and a shoe horn to maintain their shape. Keep them polished and store them in a clean dry place and you'll have happy feet for good.