You can put together a great-looking outfit--trousers, shirt, tie and jacket--and ruin it all with your shoes. A man's shoes can say a great deal about him: what are yours saying? When it comes to shoes, it's important not just to select the proper pair, but also to take good care of them. You've taken the time to launder and iron your shirt and trousers, you've selected a tie without wrinkles or stains and you got that dimple just right, but all your care so far will go for naught if you finish things off with a scuffed, dirty, worn pair of shoes. Or shoes that aren't appropriate for the outfit.
So let's start right there, with shoe selection. First off, if you're reading this, don't even think about wearing tennis or basketball or some other type of athletic shoe to work (or anywhere else) if you're not wearing a t-shirt. Are there guys who can do this? Sure, but they're not reading this site (or if they are, they don't need to be). The guys who can wear athletic shoes with their collared shirts either a) care about style and already know enough about it to break the rules and get away with it or b) don't care about style.
Assuming you're not in either of those categories, the shoe you're going to want to start with is the cap-toe oxford or derby. Here are some cap-toe oxfords:
Men's dress shoe terminology has a vocabulary all to itself, and it can get confusing. Here's a good breakdown of the key terms for our purposes. Go take a look and then come back here.
Two points from that link. First, the difference between "oxford/balmoral" and "derby/blucher" aren't very important here. Either one will be fine for your purposes, but just know that, technically, the former is considered dressier/more formal than the latter. And as the link suggested, many stores in the U.S. will refer to all of them as "oxfords," anyway, whether the lacing is open or closed. (All of the shoes shown above are true oxfords.)
Second, most guys are familiar with brogues, although they are more likely to refer to them as "wingtips." Wingtips or brogues are most closely identified with the decorative perforation patterns you usually see on such shoes.
It's common to think that the perforation patterns make the shoe more formal, but the opposite is actually true. The plainer the oxford or derby, the more formal it is. One of the reasons for this is the history of the brogue. It developed in Scotland when the Scots figured out that it would be useful to perforate their shoes to allow any water that might get in the shoe as they were hunting to run out. Because the perforations were originally added for sporting purposes, the perforations make the shoes less formal. (The shoes shown above are ordered in a way that would be considered least-to-most formal.) However, many wingtips or brogues are still formal enough for everyday wear with jacket and tie, so the choice between brogues and plainer shoes mainly comes down to personal preference.
We recommend a pair of cap-toe oxfords or derbies as our "essential" shoe because of their versatility. They will be formal enough for your jacket and tie at work, but you can also wear them with slacks or nice jeans for a date night or out on the town.
Selecting between shoe brands could be (and at some point likely will be) a whole post in itself. For now, a good place to start would be Allen Edmonds. They tend to be a pretty good value, and if you can't afford a new pair, there are many selections in good shape being sold on eBay. Great shoe values can also be found in thrift stores. Two of our pairs in heavy rotation were bought for $10 each at a local thrift store. Vintage shoes from makers such as Florsheim and Johnston & Murphy can often be found there, and their vintage lines seem better-regarded and sturdier than newer offerings from these shoe makers.
If possible, get a pair of shoes with leather soles. They are dressier, and, depending on the stitching technique (Goodyear is a good one), they can be resoled when the soles have worn out, prolonging the life of your investment.
Be sure to protect your investment by taking care of your shoes. At a minimum, get some cedar shoe trees to put into your shoes immediately after you take them off. These will help your shoes retain their proper shape, assist with the drying process, and alleviate some of the smell. You can get a couple of pairs to rotate between your shoes (their effectiveness is maximized in the first couple of hours after you take off your shoes, so no need to have trees for every pair of shoes). Nordtrom Rack has very good prices for solid trees.
Also, regularly condition your shoes. This will improve their appearance and lengthen their life even if you don't regularly polish them. But why not polish them, too? It doesn't require that much time, and it puts the finishing touch on the total presentation that you've worked diligently to assemble. (Here are some additional tips for shoe care products.)
Finally, let's address the belt, which will be the easiest advice to give in this essentials series. It should be leather, and it should reasonably approximate the color of your shoes. And that's it.
