You can pair these shoes with just about anything. The ones above are Stacy Adams, but you can find them from a variety of designers at multiple price points to fit your budget during the economic crisis (we are in recession). Like anything else I try to showcase on the site, you can get alot of use out of these so that they make for a practical investment. You want to also keep some newspaper or something durable in the insides of the shoes to preserve their shape and prevent those indentations that occur due to the natural movement of the foot from walking. These look just as great with trousers as they do with jeans. Some people like to collect sneakers or boots, but brown loafers are an essential that every aristocrat should have in the closet.
The above are from Converse but you can find canvas sneakers anywhere. And just like the loafers above, you can pair them with anything -- shorts, pants, jeans, slacks, and some people wear them with suits (I don't, but respect to those who can pull off). They are comfortable durable and they add a little urban element to another otherwise "square" outfit. These will go along way and are also a great investment.