I. Sneakers In general, you should look for sneakers that are classic and simple. There's always a risk of looking juvenile in sneakers, but you can minimize it by wearing the right ones. I recommend avoiding sneakers with more than two colors and anything that was made to play a specific sport (unless that sport was tennis in the 1950s). If you're in high school, you've got a lot more leeway here.
Low-top athletic shoes - This is a tough category, because it's easy to go wrong. If you stick to classic shoes in simple colors and avoid over-detailing and technical features, you're on the right track. J.Crew carries some New Balance and Adidas options, but you also can't go wrong with simple Nikes, New Balance 574s, Onitsuka Tigers, or Sambas. At the high end, Common Projects and MMM GATs are fantastic, but if you know what those are, you don't need this guide.
II. Casual/In-between Shoes Lots of guys focus on sneakers for casual shoes, but in almost every case, they'd be better off moving up into this category. These are shoes that are still casual (almost all of them would look great with jeans, rolled-up chinos and shorts) but look more mature than sneakers. Again, opt for classic styles with a history - it's harder to go wrong with something that's been around, virtually unchanged, for 75-100 years. These'll generally cost more than sneakers, but not as much as well-made dress shoes. In many cases, they're resoleable (like dress shoes), which extends their life dramatically.
Bucks - in white nubuck or tan suede, with a red brick sole. Classic spring/summer footwear, perfectly appropriate with jeans, go-to-hell chinos or shorts (sockless). To wear white bucks the most traditional way, you've got to go all-in preppy or pick up a seersucker suit. To use an oxymoron, white bucks are the most traditional go-to-hell shoes. Tan bucks are a little easier to wear, imo - they look great with jeans, for example. There are brighter-colored options, but not until you have other footwear basics covered.
Desert boots/chukkas - Clarks Desert Boots (CDBs) get mocked as the MFA-hivemind item, but the fact of the matter is that they're a pretty good in-between option. Beeswax leather and taupe or sand suede are the most versatile choices. Lots of other companies make chukka boots too - from low-quality $40 pairs at Kohls to $700 shell cordovan Aldens.
III. Dress Shoes
I've been stressing the classics, and that's particularly important here. Men's dress shoes have a long history and deviations from the classics almost always turn out badly (but not always). For more background information on shoe construction, here's a fantastic SF thread. SartInc has a great post on welts. Some fantastic links from a comment. Also see Esotericism's thread on the difference between a $50 shoe and a $500 shoe (hint: it's not just $450).
There are more options for narrow/wide shoes here, since high-end makers generally produce shoes in a half-dozen different widths as well as lasts that fit differently. Shoe widths go from AAA/AA/A/B/C/D(M)/E/EE/EEE/EEEE with each letter representing a 3/16" increase in width. D is the default - if width isn't listed, it's D. Measure yourself on a Brannock device for length and width, and if at all possible, try on the shoes you're planning to buy. You could try them on in a store and buy online to save some money, but in my opinion, that's a dick move.
Good dress shoes are expensive, but if you take care of them, they can easily last for a decade or more. I don't recommend paying less than $175-$200, and only that little because you can get factory seconds from Allen Edmonds for about that price. In general, you should budget $250+ for dress shoes. If that's out of your budget, then consider buying used (on ebay or the SF B&S forum) or resigning yourself to a pair that won't last nearly as long. Florsheim and Johnston & Murphy make lower-priced ($100-$175) dress shoes in classic style, but in my opinion, it's worth waiting and saving for better shoes.
Instead of a list of models and styles, I'm going to organize this based on decisions to be made and variations among shoes -
Color - This decision is not quite a simple as black vs. brown, although that's the core of it. Black shoes aren't as versatile - you'll want to save them for black and charcoal suits (and navy, in very conservative environments). Generally, stick with a plain toe or captoe for black, since you'll be wearing them in a conservative or formal situation. Black wingtips are an odd contradiction. Brown shoes are much more versatile - here's a guide from PTO that gives a little more information, but what it doesn't say is that brown dress shoes can often be dressed down with dark jeans or chinos too. The challenge of brown is that there isn't a single shade, although generally speaking, the lighter the shade the more casual the shoe. Using AE as an example, tan is more casual than walnut, which is more casual than dark brown, which is more casual than burgundy or merlot (I'm referring only to color here - ignore the styles in these examples).
Type of Leather - One of the main reasons to avoid cheap dress shoes is because they're made with cheap, bad leather. Those $50 Dockers shoes from Kohl's are corrected-grain leather with a plastic top-coat to hide the quality (if they're even real leather). They're going to look terrible fast. On the other hand, full-grain leather (or shell cordovan) will look better as it ages and gets character. Most companies make a version of their longwings/wingtips/captoes/plaintoes in suede (sometimes even crazy colors of suede), but those belong in the in-betweener category. You could pair suede longwings with a tweed suit, heavyweight wool pants, or chinos, but they rarely look good with a traditional navy or charcoal suit.
Lacing Style - Open-laced derbies/bluchers are more casual than closed-lace oxfords/balmorals. If you want a shoe you can wear with a suit and jeans/chinos, go for a blucher. Be aware that bluchers with a suit makes some people cringe, but 98% won't notice. Some shoes use a monk strap instead of laces - some even double up on the monk straps. There are even trip-monks, but we're getting into ridiculous Gillette-razor-like territory now. Saddle shoes, which have gotten more popular the last few years after being out of style for a long time, are almost always balmorals but they should be worn casually.
Toe design - Here's the biggest, most obvious difference between shoes. Your main choices (from most to least casual) are longwings, wingtips, captoes, and plain-toes. Longwings and wingtips will almost always have broguing (those little holes punches in the leather) which makes them more casual. Captoe brogues are more casual than plain captoes, and plaintoes with a medallion are more casual than plaintoes without. The other big distinction here is the overall shape of the toe box. Round toes are classic (because they're the most flattering to the foot's natural shape), chisel toes are more modern and sleek, and square toes are to be avoided. Also think about the overall height of the toe box - too much volume looks cheap and bulbous, too little volume looks cramped. Aim for a middle ground.
Soles - For anything you're planning to wear with a suit, you want leather soles. Rubber soles almost always look clunky and cheap (although there are some exceptions, but they're niche shoes). If you live in an area with a lot of rain, you could have a cobbler apply a thin layer of rubber topy to your soles or get a pair of overshoes. Alternatively, just wear boots to the office, carry your shoes in a bag and change when you get there.
Opera pumps - You'll never need them, but in the interest of being thorough, there they are.
Avoid - square toes and bicycle-stitched toes, both of which are unflattering and dated. Slip-ons like this are the uniform of the terribly-dressed. Here's why. Avoid cheap, shiny leather if you want your shoes to last. It's the lowest-quality stuff that can legally be called leather, and covered with a plastic finish. It'll crinkle, crease and look terrible in less than a month. These aren't real shoes - they're shoe-like objects. Finally, avoid too much extraneous detail stitching - which seems ironic, given that I recommended longwings and brogues. The difference is that those shoes have an established history - these don't. That seems like an arbitrary line to draw, but there it is. Not everything makes sense.
IV. Care and Storage
If you want your shoes to last and look good as age, you need to take care of them properly. Valet has a great visual guide to basic dress shoe care - basically, let them dry out between wearings, use cedar shoe trees, and buff/polish regularly. Avoid plastic shoe trees, which will help your shoes hold their shape but won't dry them out. Cedar shoe trees are $10-20/pr at places like DSW and Nordstrom Rack, and there's no better investment you can make in your nice shoes.
Once you've worn your shoes for 4-6 years, it might be time to have them resoled. Companies like Allen Edmonds, Alden, Quoddy, and most major manufacturers will do this for their own shoes, but your local cobbler could resole just about any pair of shoes. If you don't have a local cobbler, I've heard nothing but praise for B.Nelson Shoes, who will do resoles and repairs by mail-order. Expect to pay $50-75 for this kind of service. For shoes that need more than a simple resole, you may need a full recrafting. Allen Edmonds and Alden will do it for their own shoes, and again, places like B.Nelson will work on any pair. Here's an example of what you could expect. The cost is about $125-150.
You don't need trees for sneakers and other casual shoes, but you should clean them regularly. Water, a toothbrush, and/or a Magic Eraser will keep sneakers clean enough. Don't be meticulous about it though - I don't know why, but there's nothing quite as sad as a middle-aged guy in a brand-new, squeaky-clean pair of sneakers. Leave beat-to-shit Chucks to the middle-school version of yourself though. Aim for the middle ground.
For suede shoes, Simple Threads has a good guide. So does Put This On.
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